EP1815273A2 - Curable high refractive index resins for optoelectronic applications - Google Patents
Curable high refractive index resins for optoelectronic applicationsInfo
- Publication number
- EP1815273A2 EP1815273A2 EP20050858173 EP05858173A EP1815273A2 EP 1815273 A2 EP1815273 A2 EP 1815273A2 EP 20050858173 EP20050858173 EP 20050858173 EP 05858173 A EP05858173 A EP 05858173A EP 1815273 A2 EP1815273 A2 EP 1815273A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- individually selected
- composition
- hydrogen
- cycloaliphatics
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 230000005693 optoelectronics Effects 0.000 title claims description 7
- 229920005989 resin Polymers 0.000 title abstract description 27
- 239000011347 resin Substances 0.000 title abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 224
- 238000000034 method Methods 0.000 claims abstract description 76
- 125000003118 aryl group Chemical group 0.000 claims abstract description 49
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 239000000758 substrate Substances 0.000 claims abstract description 20
- 238000004132 cross linking Methods 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 39
- 235000012239 silicon dioxide Nutrition 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 239000011521 glass Substances 0.000 claims description 27
- 239000010453 quartz Substances 0.000 claims description 27
- 229910052710 silicon Inorganic materials 0.000 claims description 27
- 239000010703 silicon Substances 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 150000002431 hydrogen Chemical class 0.000 claims description 25
- 229910002601 GaN Inorganic materials 0.000 claims description 12
- 229910005540 GaP Inorganic materials 0.000 claims description 12
- JMASRVWKEDWRBT-UHFFFAOYSA-N Gallium nitride Chemical compound [Ga]#N JMASRVWKEDWRBT-UHFFFAOYSA-N 0.000 claims description 12
- HZXMRANICFIONG-UHFFFAOYSA-N gallium phosphide Chemical compound [Ga]#P HZXMRANICFIONG-UHFFFAOYSA-N 0.000 claims description 12
- 229910052738 indium Inorganic materials 0.000 claims description 12
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910001218 Gallium arsenide Inorganic materials 0.000 claims description 6
- 229910000530 Gallium indium arsenide Inorganic materials 0.000 claims description 6
- 229910052581 Si3N4 Inorganic materials 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 6
- KXNLCSXBJCPWGL-UHFFFAOYSA-N [Ga].[As].[In] Chemical compound [Ga].[As].[In] KXNLCSXBJCPWGL-UHFFFAOYSA-N 0.000 claims description 6
- 229920006397 acrylic thermoplastic Polymers 0.000 claims description 6
- FTWRSWRBSVXQPI-UHFFFAOYSA-N alumanylidynearsane;gallanylidynearsane Chemical compound [As]#[Al].[As]#[Ga] FTWRSWRBSVXQPI-UHFFFAOYSA-N 0.000 claims description 6
- AJGDITRVXRPLBY-UHFFFAOYSA-N aluminum indium Chemical compound [Al].[In] AJGDITRVXRPLBY-UHFFFAOYSA-N 0.000 claims description 6
- 239000000919 ceramic Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 150000002739 metals Chemical class 0.000 claims description 6
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 6
- 239000000123 paper Substances 0.000 claims description 6
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 6
- 229920000515 polycarbonate Polymers 0.000 claims description 6
- 239000004417 polycarbonate Substances 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 6
- 229920002635 polyurethane Polymers 0.000 claims description 6
- 239000004814 polyurethane Substances 0.000 claims description 6
- 239000000377 silicon dioxide Substances 0.000 claims description 6
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 claims description 6
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000002834 transmittance Methods 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 230000005540 biological transmission Effects 0.000 abstract description 48
- 238000000576 coating method Methods 0.000 abstract description 30
- -1 aromatic epoxides Chemical class 0.000 abstract description 9
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 abstract description 8
- 150000002118 epoxides Chemical class 0.000 abstract description 4
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 abstract description 4
- 150000002921 oxetanes Chemical class 0.000 abstract description 3
- 150000002989 phenols Chemical class 0.000 abstract description 2
- 150000003573 thiols Chemical class 0.000 abstract description 2
- 238000009472 formulation Methods 0.000 description 83
- 239000010410 layer Substances 0.000 description 48
- 238000002360 preparation method Methods 0.000 description 42
- 235000012431 wafers Nutrition 0.000 description 42
- 239000000463 material Substances 0.000 description 27
- 239000011248 coating agent Substances 0.000 description 23
- 238000004528 spin coating Methods 0.000 description 23
- 229910052724 xenon Inorganic materials 0.000 description 23
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 23
- 239000003921 oil Substances 0.000 description 22
- 238000003848 UV Light-Curing Methods 0.000 description 21
- 230000001133 acceleration Effects 0.000 description 21
- 238000004458 analytical method Methods 0.000 description 21
- 230000008033 biological extinction Effects 0.000 description 21
- 230000009977 dual effect Effects 0.000 description 21
- 238000001392 ultraviolet--visible--near infrared spectroscopy Methods 0.000 description 21
- 238000003756 stirring Methods 0.000 description 18
- 239000004593 Epoxy Substances 0.000 description 17
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 16
- 239000003085 diluting agent Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 239000004615 ingredient Substances 0.000 description 13
- 238000002156 mixing Methods 0.000 description 12
- 229920002274 Nalgene Polymers 0.000 description 10
- 239000003822 epoxy resin Substances 0.000 description 10
- 229920003986 novolac Polymers 0.000 description 10
- 229920000647 polyepoxide Polymers 0.000 description 10
- 230000003287 optical effect Effects 0.000 description 6
- 101001133946 Tropidechis carinatus Acidic phospholipase A2 5 Proteins 0.000 description 5
- LMIOYAVXLAOXJI-UHFFFAOYSA-N 3-ethyl-3-[[4-[(3-ethyloxetan-3-yl)methoxymethyl]phenyl]methoxymethyl]oxetane Chemical compound C=1C=C(COCC2(CC)COC2)C=CC=1COCC1(CC)COC1 LMIOYAVXLAOXJI-UHFFFAOYSA-N 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 102100033806 Alpha-protein kinase 3 Human genes 0.000 description 1
- 101710082399 Alpha-protein kinase 3 Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical class C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000003491 array Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/10—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers containing more than one epoxy radical per molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/226—Mixtures of di-epoxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/38—Epoxy compounds containing three or more epoxy groups together with di-epoxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/16—Cyclic ethers having four or more ring atoms
- C08G65/18—Oxetanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L63/04—Epoxynovolacs
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L63/08—Epoxidised polymerised polyenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L63/10—Epoxy resins modified by unsaturated compounds
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/80—Constructional details
- H10K59/875—Arrangements for extracting light from the devices
- H10K59/879—Arrangements for extracting light from the devices comprising refractive means, e.g. lenses
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/85—Arrangements for extracting light from the devices
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
Definitions
- the present invention is broadly concerned with novel compositions that can be formed into high refractive index layers.
- the compositions are useful for forming solid- state devices such as flat panel displays, optical sensors, integrated optical circuits, light- emitting diodes (LEDs), microlens arrays, and optical storage disks.
- High refractive index coatings offer a improved performance in the operation of many optoelectronic devices. For example, the efficiency of LEDs is improved by applying a layer of high refractive index material between the device and the encapsulating material, thereby reducing the refractive index mismatch between the semiconductor substrate and the surrounding encapsulating plastic.
- a higher refractive index material also allows lenses to have a higher numerical aperture (NA), which leads to increased performance.
- UV- curable resins are based on free radical polymerization. This method, while allowing for rapid curing, is sensitive to the presence of oxygen.
- Optically clear epoxy resins are mostly cured by thermal methods, have long cure times, or suffer from short pot lives.
- the present invention overcomes these problems by providing novel compositions having high refractive indices and useful in the fabrication of optoelectronic components.
- the compositions broadly comprise a reactive solvent system (e.g., aromatic resin functionalized with one or more reactive groups such as epoxides, vinyl ethers, oxetanes) that dissolve a reactive high refractive index component such as aromatic epoxides, vinyl ethers, oxetanes, phenols, or thiols.
- a reactive solvent system e.g., aromatic resin functionalized with one or more reactive groups such as epoxides, vinyl ethers, oxetanes
- a reactive high refractive index component such as aromatic epoxides, vinyl ethers, oxetanes, phenols, or thiols.
- composition comprises a compound (I) having a formula selected from the group consisting of
- each R is individually selected from the group consisting of hydrogen, alkyls
- alkoxys preferably from about C 1 -C 100 , more preferably from about C 1 -C 50 , and even more preferably from about C 1 -C 12
- cycloaliphatics preferably from about C 3 -C 100 , more preferably from about C 3 -C 12 , and even more preferably from about
- each B is individually selected from the group consisting of -CO-, -COO-,
- x is from about 0-6; and n is from about 0-100, preferably from about 1-50, and even more preferably from about 1-40.
- Aromatic Moieties I include those selected from the group consisting of
- Aromatic Moieties II include those selected from the group consisting of
- Aromatic Moieties III include those selected from the group consisting of
- each R' is individually selected from the group consisting of -C(CR"' 3 ) 2 -, -CR'" 2 -, -SO 2 -, -S-, -SO- and -CO-, where each R'" is individually selected from the group consisting of hydrogen, alkyls (preferably from about C 1 -Ci 00 , more preferably from about C 1 -C 20 , and even more preferably from about C 1 - C 12 ), alkoxys (preferably from about C 1 -C 100 , more preferably from about C 1 -C 50 , and even more preferably from about C 1 -C 12 ), cycloaliphatics (preferably from about C 3 -C 100 , more preferably from about C 3 -C 12 , and even more preferably from about C 5 -C 12 ), and aromatics (preferably from about C 3
- a reactive solvent is one that reacts with the other compounds in the composition so as to be substantially (i.e., at least about 95% by weight, preferably at least about 99% by weight, and even more preferably about 100% by weight) consumed during the subsequent polymerization and crosslinking reactions.
- the reactive solvent also functions to dissolve the other ingredients in the composition to assist in homogenizing the composition.
- m will be at least 1.
- the X group be present in the compound to provide at least about 1% by weight X groups, more preferably from about 5-80% by weight X groups, and even more preferably from about 30-70% by weight X groups, based upon the total weight of the composition taken as 100% by weight.
- the composition will comprise both the compound as a reactive solvent (i.e., without X groups) and as a high refractive index material (i.e., with X groups).
- the reactive solvent compound be present at levels of at least about 1% by weight, preferably from about 5-95% by weight, and even more preferably from about 10-50% by weight, based upon the total weight of the composition taken as 100% by weight.
- the high refractive index compound is preferably present at levels of at least about 1% by weight, preferably from about 5-95% by weight, and even more preferably from about 10-90% by weight, based upon the total weight of the composition taken as 100% by weight.
- the composition also preferably comprises a crosslinking catalyst.
- Preferred crosslinking catalysts are selected from the group consisting of acids, photoacid generators (preferably cationic), photobases, thermal acid generators, thermal base generators, and mixtures thereof.
- Examples of particularly preferred crosslinking catalysts include those selected from the group consisting of substituted trifunctional sulfonium salts (preferably where at least one functional group is an aryl group), iodonium salts, disulfones, triazines, diazomethanes, and sulfonates.
- the crosslinking catalyst should be included at levels of from about 1-15% by weight, preferably from about 1-10% by weight, and even more preferably from about 1 -8% by weight, based upon the total weight of the reactive solvent and high refractive index material taken as 100% by weight.
- composition preferably further comprises a compound selected from the group consisting of
- each R" is individually selected from the group consisting of -CR'" 2 -, -SO 2 -, -SO-, -S-, -0-, -CO-, and -NR"'-, where each R'" is individually selected from the group consisting of hydrogen, alkyls (preferably from about C 1 -C 100 , more preferably from about C 1 -C 20 , and even more preferably from about C 1 - C 12 ), alkoxys (preferably from about C 1 -Cj 00 , more preferably from about C 1 -C 20 , and even more preferably from about C 1 -C 12 ), cycloaliphatics (preferably from about C 3 -C 100 , more preferably from about C 3 -C 12 , and even more preferably from about C 5 -C 12 ), and aromatics (preferably from about C 3 -C 100 , more preferably from about C 3 -C 50 , and even more preferably from about C 5 -C 12 ); each X
- the composition comprises very low levels of non-reactive solvents or diluents (e.g., PGME, PGMEA, propylene carbonate).
- non-reactive solvents or diluents e.g., PGME, PGMEA, propylene carbonate.
- the composition comprises less than about 5% by weight, preferably less than about 2% by weight, and even more preferably about 0% by weight non-reactive solvents or diluents, based upon the total weight of the composition taken as 100% by weight.
- other optional ingredients can be included in the inventive compositions as well. Examples of some optional ingredients include fillers, UV stabilizers, and surfactants.
- the inventive compositions are formed by heating the reactive solvent compound(s) until it achieves a temperature of from about 20- 100 0 C, and more preferably from about 60-80 0 C.
- the high refractive index compound(s) are then added and mixing is continued until a substantially homogeneous mixture is obtained.
- the crosslinking catalyst and any other optional ingredients are then added and mixing is continued.
- compositions are applied to a substrate by any known method to form a coating layer or film thereon. Suitable coating techniques include dip coating, roller coating, inj ection molding, film casting, draw-down coating, or spray coating.
- a preferred method involves spin coating the composition onto the substrate at a rate of from about 500-5,000 rpm (preferably from about 1,000-4,000 rpm) for a time period of from about 30-480 seconds (preferably from about 60-300 seconds) to obtain uniform films.
- Substrates to which the coatings can be applied include those selected from the group consisting of silicon, silicon dioxide, silicon nitride, aluminum gallium arsenide, aluminum indium gallium phosphide, gallium nitride, gallium arsenide, indium gallium phosphide, indium gallium nitride, indium gallium arsenide, aluminum oxide (sapphire), glass, quartz, polycarbonates, polyesters, acrylics, polyurethanes, papers, ceramics, and metals (e.g., copper, aluminum, gold).
- the applied coatings are then cured by either baking or exposing to light having a wavelength effective for crosslinking the resin within the composition, depending upon the catalyst system utilized.
- the composition will be baked at temperatures of at least about 40 0 C, and more preferably from about 50-150 0 C for a time period of at least about 5 seconds (preferably from about 10-60 seconds).
- Light exposure is the most preferred method of effecting curing of the composition because the most preferred inventive compositions are photocurable.
- this curing method light (e.g., at a wavelength of from about 100-1,000 nm (more preferably from about 240-400 nm) or at an exposure energy of from about 0.005-20 J/cm 2 (more preferably from about 0.1-10 J/cm 2 ) is used to generate the acid that catalyzes the polymerization and crosslinking reactions.
- Cured coatings prepared according to the instant invention will have superior properties, and can be formulated to have thicknesses of from about 1-5,000 ⁇ m.
- the cured coatings will have a refractive index of at least about 1.5, preferably at least about 1.56, and more preferably at least about 1.60, at wavelengths of from about 375-1 ,700 nm.
- cured coatings having a thickness of about 100 ⁇ m will have a percent transmittance of at least about 80%, preferably at least about 90%, and even more preferably least about 95% at wavelengths of from about 375-1700 nm.
- Figure 1 is a graph depicting the n and k values for a cured layer formed from the composition of Example 1;
- Fig. 2 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 1;
- Figs . 3 -3 d are graphs demonstrating the light stability at different energy levels of a cured layer formed from the composition of Example 1;
- Figs.4-4c are graphs demonstrating the thermal stability over time of a cured layer formed from the composition of Example 1;
- Fig. 5 is a graph depicting the n and k values for a cured layer formed from the composition of Example 2;
- Fig. 6 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 2;
- Figs. 7-7c are graphs demonstrating the light stability at different energy levels of a cured layer formed from the composition of Example 2;
- Figs. 8-8c are graphs demonstrating the thermal stability over time of a cured layer formed from the composition of Example 2;
- Fig. 9 is a graph depicting the n and k values for a cured layer formed from the composition of Example 3.
- Fig. 10 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 3;
- Fig. 11 is a graph depicting the n and k values for a cured layer formed from the composition of Example 4.
- Fig. 12 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 4;
- Fig. 13 is a graph depicting the n and k values for a cured layer formed from the composition of Example 5;
- Fig. 14 is a graph showing the percent oflight transmission of a cured layer formed from the composition of Example 5;
- Fig. 15 is a graph depicting the n and k values for a cured layer formed from the composition of Example 6;
- Fig. 16 is a graph showing the percent oflight transmission of a cured layer formed from the composition of Example 6;
- Fig. 17 is a graph depicting the n and k values for a cured layer formed from the composition of Example 7;
- Fig. 18 is a graph showing the percent oflight transmission of a cured layer formed from the composition of Example 7;
- Fig. 19 is a graph depicting the n and k values for a cured layer formed from the composition of Example 8.
- Fig.20 is a graph showing the percent oflight transmission of a cured layer formed from the composition of Example 8;
- Fig. 21 is a graph depicting the n and k values for a cured layer formed from the composition of Example 9;
- Fig.22 is a graph showing the percent oflight transmission of a cured layer formed from the composition of Example 9;
- Fig. 23 is a graph depicting the n and k values for a cured layer formed from the composition of Example 10;
- Fig.24 is a graph showing the percent oflight transmission of a cured layer formed from the composition of Example 10.
- Fig. 25 is a graph depicting the n and k values for a cured layer formed from the composition of Example 11;
- Fig.26 is a graph showing the percent oflight transmission of a cured layer formed from the composition of Example 11;
- Fig. 27 is a graph depicting the n and k values for a cured layer formed from the composition of Example 12;
- Fig.28 is a graph showing the percent oflight transmission of a cured layer formed from the composition of Example 12
- Fig. 29 is a graph depicting the n and k values for a cured layer formed from the composition of Example 13;
- Fig. 30 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 13;
- Fig. 31 is a graph depicting the n and k values for a cured layer formed from the composition of Example 14;
- Fig. 32 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 14;
- Fig. 33 is a graph depicting the n and k values for a cured layer formed from the composition of Example 15;
- Fig. 34 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 15;
- Fig. 35 is a graph depicting the n and k values for a cured layer formed from the composition of Example 16;
- Fig.36 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 16;
- Fig. 37 is a graph depicting the n and k values for a cured layer formed from the composition of Example 17;
- Fig.38 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 17;
- Fig. 39 is a graph depicting the n and k values for a cured layer formed from the composition of Example 18;
- Fig.40 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 18;
- Fig. 41 is a graph depicting the n and k values for a cured layer formed from the composition of Example 19;
- Fig.42 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 19;
- Fig. 43 is a graph depicting the n and k values for a cured layer formed from the composition of Example 20;
- Fig.44 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 20;
- Fig. 45 is a graph depicting the n and k values for a cured layer formed from the composition of Example 21.
- Fig.46 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 21.
- Formulation 1 could be coated onto various types of wafers (silicon, quartz, glass, etc.).
- a typical spin-coating and UV-curing process is described in the following:
- a CEE 1 OOCB Spinner/Hotplate (Brewer Science Inc.) was used. Spin speeds ranged from 1,000-5,000 rpm. Acceleration ranged from 500-20,000 rpm/sec. Spin times ranged from 90-360 seconds.
- a Canon PLA-501F Parallel Light Mask Aligner with xenon lamp was used to cure the films. Output was 3.7 mJ-sec/cm 2 at 365 run. Exposure times ranged from 10-12 minutes. Total exposure doses ranged from 1.2- 2.7 J/cm 2 .
- Table 1 below shows representative film processing data specifically for these materials.
- Refractive index (n) and extinction coefficient (k) data were obtained using a variable angle spectroscopic ellipsometer (VASE, H-VASE, J.A. Woollam Company).
- a Varian Gary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer was used to measure the light transmission quality of the films.
- the mode used was nanometers, with a range of 200 to 3,300 nm.
- the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/rnin.
- the baseline parameter was zerc ⁇ aseline.
- the graph of Fig. 2 shows the percent of light transmission (%T) of the films obtained using the parameters described above.
- the refractive index (n) and extinction coefficient (k) data were obtained using a variable angle spectroscopic ellipsometer (VASE, H-VASE, J.A.
- the transmission data of the films shown in the graph of Fig. 6 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer.
- the mode used was nanometers, with a range of 200-3,300 nm.
- the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min.
- the baseline parameter was zero/baseline.
- the thermal stability of the film was investigated using a Blue M Electric Company Convection Oven, Model ESP-400BC-4, and subjecting the cured films to a temperature of 100 °C for 6 days.
- the film transmission, expressed as a percentage, is shown in Fig. 8.
- the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.).
- a CEE IOOCB Spinner/Hotplate was used to apply Formulation 3 to wafers. Spin speed was 1,000-5000 rpm, acceleration was 4,500 rpm/sec, and spin time was 60 seconds.
- a Canon PLA-501F Parallel Light Mask Aligner with xenon lamp was used.
- the output was 2.7 mJ-sec/cm 2 at 365 nm, the time was 12 minutes, and the total exposure dose was 2.0 J/cm 2 .
- the refractive index (n) and extinction coefficient (k) data were obtained using a variable angle spectroscopic ellipsometer (VASE, H-VASE, J.A. Woollam Company).
- the transmission data of the films shown in the graph of Fig. 10 and expressed as a percentage, were obtained using a Varian Gary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer.
- the mode used was nanometers, with a range of 300-3,300 nm.
- the average time was 0.1 second
- the data interval was 1.0 nm
- the scan rate was 600 nm/min.
- Y max 100.00.
- the baseline parameter was zero/baseline.
- VECTOMER 4010 (available from Morflex) were added dropwise.
- the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.).
- a CEE IOOCB Spinner/Hotplate was used to apply Formulation 4 to wafers. The spin speed was 1,000 - 5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 60 seconds. The films were then baked for 6 sec at 112 0 C.
- a Canon PLA-5 OIF Parallel Light Mask Aligner with xenon lamp was used to cure the films.
- the output was 2.7 mJ-sec/cm 2 at 365 nm, the time was 9 minutes, and the total exposure dose was 1.5 J/cm 2 .
- the refractive index (n) and extinction coefficient (k) data were obtained using a variable angle spectroscopic ellipsometer (VASE, H-VASE, J.A. Woollam Company).
- the mode used was nanometers, with a range of 300-3,300 nm.
- the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min.
- the baseline parameter was zero/baseline.
- the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.).
- a CEE IOOCB Spinner/Hotplate was used to apply Formulation 5 to wafers.
- the spin speed was 1,000- 5,000 rpm
- the acceleration was 4,500 rpm/sec
- the spin time was 60 seconds.
- a Canon PLA-50 IF Parallel Light Mask Aligner with xenon lamp was used to cure the firms.
- the output was 2.7 mJ-sec/cm 2 at 365 nm, the time was 12 minutes, and the total exposure dose was 2.0 J/cm 2 .
- the refractive index (n) and extinction coefficient (k) data were obtained using a variable angle spectroscopic ellipsometer (VASE, H-VASE, J.A. Woollam Company).
- the mode used was nanometers, with a range of 300-3,300 nm.
- the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min.
- the baseline parameter was zero/baseline.
- the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.).
- a CEE IOOCB Spinner/Hotplate was used to apply Formulation 6 to wafers.
- the Spin speed was 1,000 - 5,000 rpm
- the acceleration was 4,500 rpm/sec
- the spin time was 360 seconds.
- a Canon PLA-50 IF Parallel Light Mask Aligner with xenon lamp was used to cure the films.
- the output was 2.7 mJ-sec/cm 2 at 365 nm, the time was 12 minutes, and the total exposure dose was 2.0 J/cm 2 .
- the refractive index (n) and extinction coefficient (k) data were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J.A. Woollam Company).
- the mode used was nanometers, with a range of 300-3,300 nm.
- the average time was 0.1 second
- the data interval was 1.0 nm
- the scan rate was 600 nrn/min.
- the baseline parameter was zero/baseline.
- the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.).
- a CEE IOOCB Spinner/Hotplate was used to apply Fo ⁇ nulation 7 to wafers. Spin speed was 1,000 - 5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 360 seconds.
- a Canon PLA-501 F Parallel Light Mask Aligner with xenon lamp was used to cure the films.
- the output was 2.7 mJ-sec/cm 2 at 365 nm, the time was 12 minutes, and the total exposure dose was 2.0 J/cm 2 .
- the refractive index (n) and extinction coefficient (k) data were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J.A. Woollam Company).
- the transmission data of the films shown in the graph of Fig. 18 and expressed as a percentage, were obtained using a Varian Gary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer.
- the mode used was nanometers, with a range of 300-3,300 nm.
- the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min.
- the baseline parameter was zero/baseline.
- An oil bath was preheated to 80 ° C (oil temperature) .
- the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.).
- a CEE IOOCB Spinner/Hotplate was used to apply Formulation 8 to wafers.
- the spin speed was 1,000- 5,000 rpm
- the acceleration was 4,500 rpm/sec
- the spin time was 60 seconds.
- a Canon PLA-50 IF Parallel Light Mask Aligner with xenon lamp was used to cure the films.
- the output was 2.7 mJ-sec/cm 2 at 365 nm, the time was 12 minutes, and the total exposure doses was 2.0 J/cm 2 .
- the refractive index (n) and extinction coefficient (k) data were obtained using a variable angle spectroscopic ellipsometer (VASE, H-VASE, J.A.
- the transmission data of the films shown in the graph of Fig.20 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer.
- the mode used was nanometers, with a range of 300-3,300 nm.
- the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min.
- the baseline parameter was zero/baseline.
- the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.).
- a CEE IOOCB Spinner/Hotplate was used to apply Formulation 9 to wafers.
- the spin speed was 1,000- 5,000 rpm
- the acceleration was 4,500 rpm/sec
- the spin time was 360 seconds.
- a Canon PLA-50 IF Parallel Light Mask Aligner with xenon lamp was used to cure the films.
- the output was 2.7 mJ-sec/cm 2 at 365 nm, the time was 12 minutes, and the total exposure dose was 2.0 J/cm 2 .
- the refractive index (n) and extinction coefficient (k) data were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J.A. Woollam Company).
- the transmission data of the films shown in the graph of Fig. 22 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer.
- the mode used was nanometers, with a range of 300-3,300 nm.
- the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min.
- the baseline parameter was zero/baseline.
- the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.).
- a CEE IOOCB Spinner/Hotplate was used to apply Formulation 10 to wafers. Spin speed was 1,000- 5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 360 seconds.
- a Canon PLA-5 OIF Parallel Light Mask Aligner with xenon lamp was used to cure the films.
- the output was 2.7 mJ-sec/cm 2 at 365 nm, the time was 7.5 minutes, and the total exposure dose was 1.2 J/cm 2 .
- the refractive index (n) and extinction coefficient (k) data were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J.A. Woollam Company).
- the mode used was nanometers, with a range of 300-3,300 nm.
- the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min.
- the baseline parameter was zero/baseline.
- the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.).
- a CEE IOOCB Spinner/Hotplate was used to apply Formulation 11 to wafers.
- the spin speed was 1,000- 5,000 rpm
- the acceleration was 4,500 rpm/sec
- the spin time was 60 seconds.
- a Canon PLA-5 OIF Parallel Light Mask Aligner with xenon lamp was used to cure the films.
- the output was 2.7 mJ-sec/cm 2 at 365 nm, the time was 7.5 minutes, and the total exposure dose was 1.2 J/cm 2 .
- the refractive index (n) and extinction coefficient (k) data were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J.A. Woollam Company).
- the transmission data of the films shown in the graph of Fig. 26 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer.
- the mode used was nanometers, with a range of 300-3300 nm.
- the average time was 0.1 second
- the data interval was 1.0 nm
- the scan rate was 600 nm/min.
- Y max 100.00.
- the baseline parameter was zero/baseline.
- the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.).
- a CEE IOOCB Spinner/Hotplate was used to apply Formulation 12 to wafers.
- the spin speed was 1 ,000-
- the refractive index (n) and extinction coefficient (k) data were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J.A. Woollam Company).
- the transmission data of the films shown in the graph of Fig.28 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer.
- the mode used was nanometers, with a range of 300-3,300 nm.
- the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min.
- the baseline parameter was zero/baseline.
- the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.).
- a CEE IOOCB Spinner/Hotplate was used to apply Formulation 13 to wafers .
- the spin speed was 1,000- 5,000 rpm
- the acceleration was 4,500 rpm/sec
- the spin time was 60 seconds.
- a CanonPLA-50 IF Parallel Light Mask Aligner with xenon lamp was used to cure the films.
- the output was 2.7 mJ-sec/cm 2 at 365 nm, the time was 12 minutes, and the total exposure doses was 2.0 J/cm 2 .
- the refractive index (n) and extinction coefficient (k) data were obtained using a variable angle spectroscopic ellipsometer (VASE, H-VASE, J. A.
- the transmission data of the films shown in the graph of Fig. 30 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer.
- the mode used was nanometers, with a range of 300-3,300 nm.
- the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min.
- the baseline parameter was zero/baseline.
- the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.).
- a CEE IOOCB Spinner/Hotplate was used to apply formulation 14 to wafers. The spin speed was 1,000- 5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 60 seconds.
- a Canon PLA-501 F Parallel Light Mask Aligner with xenon lamp was used to cure the films.
- the output was 2.7 mJ-sec/cm 2 at 365 nm, the time was 37 minutes, and the total exposure dose was 6.03 J/cm 2 .
- the refractive index (n) and extinction coefficient (k) data were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J.A. Woollam Company).
- the transmission data of the films shown in the graph of Fig. 32 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer.
- the mode used was nanometers, with a range of 300-3,300 nm.
- the average time was 0.1 second
- the data interval was 1.0 nm
- the scan rate was 600 nm/min.
- Y max 100.00.
- the baseline parameter was zero/baseline.
- a Canon PLA-5 OIF Parallel Light Mask Aligner with xenon lamp was used to cure the films.
- the output was 2.7 mJ-sec/cm 2 at 365 nm, the time was 12 minutes, and the total exposure dose was 2.0 J/cm 2 .
- the refractive index (n) and extinction coefficient (k) data of Fig.33 were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J.A. Woollam Company).
- the transmission data of the films shown in the graph of Fig. 34 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer.
- the mode used was nanometers, with a range of 300-3300 nm.
- the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min.
- the baseline parameter was zero/baseline.
- the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.).
- a CEE IOOCB Spinner/Hotplate was used to apply Formulation 16 to wafers. The spin speed was 1 ,000-
- a Canon PLA-50 IF Parallel Light Mask Aligner with xenon lamp was used to cure the films.
- the output was 2.7 mJ-sec/cm 2 at 365 nm, the time was 14.5 minutes, and the total exposure dose was 2.3 J/cm 2 .
- Representative film processing data for these materials are shown in Table 31.
- Table 32 The data of Table 32 were obtained through the analysis of the above films by using a prism coupler (Metricon 2010). Table 32
- the refractive index (n) and extinction coefficient (k) data were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J. A.
- the transmission data of the films shown in the graph of Fig. 36 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer.
- the mode used was nanometers, with a range of 300-3,300 nm.
- the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min.
- the baseline parameter was zero/baseline.
- EXAMPLE 17 A Curable High Refractive Index Resin Prepared with a Brominated Epoxy Resin and an Epoxy Novolac A. Preparation of Formulation 17
- the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.).
- a CEE IOOCB Spinner/Hotplate was used to apply Formulation 17 to wafers.
- the spin speed was 1 ,000- 5,000 rpm
- the acceleration was 4,500 rpm/sec
- the spin time was 60 seconds.
- a Canon PLA-5 OIF Parallel Light Mask Aligner with xenon lamp was used to cure the films.
- the output was 2.7 mJ-sec/cm 2 at 365 run, the time was 12 minutes, and the total exposure dose was 1.9 J/cm 2 .
- the refractive index (n) and extinction coefficient (k) data were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J.A. Woollam Company).
- the transmission data of the films shown in the graph of Fig. 38 and expressed as a percentage, were obtained using a Varian Gary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer.
- the mode used was nanometers, with a range of 300-3,300 nm.
- the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min.
- the baseline parameter was zero/baseline.
- the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.).
- a CEE IOOCB Spinner/Hotplate was used to apply Formulation 18 to wafers. Spin speed was 1,000- 5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 60 seconds.
- a Canon PLA-501 F Parallel Light Mask Aligner with xenon lamp was used to cure the films. The output was 2.7 mJ-sec/cm 2 at 365 nm, the time was 14 minutes, and the total exposure doses was 2.3 J/cm 2 .
- the refractive index (n) and extinction coefficient (k) data were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J.A. Woollam Company) .
- the transmission data of the films shown in the graph of Fig.40 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer.
- the mode used was nanometers, with a range of 300-3,300 nm.
- the average time was 0.1 second
- the data interval was 1.0 nm
- the scan rate was 600 nm/min.
- Y max 100.00.
- the baseline parameter was zero/baseline.
- the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.).
- a CEE IOOCB Spinner/Hotplate was used to apply Formulation 19 to wafers.
- the spin speed was 1 ,000- 5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 60 seconds.
- a Canon PLA-501 F Parallel Light Mask Aligner with xenon lamp was used to cure the films.
- the output was 2.7 mJ-sec/cnr at 365 nm, the time was 12 minutes, and the total exposure doses was 2 J/cm 2 .
- Table 38 The data of Table 38 were obtained through the analysis of the above films by using a prism coupler (Metricon 2010). Table 38
- the refractive index (n) and extinction coefficient (k) data were obtained using a variable angle spectroscopic ellipsometer (VASE, H-VASE, J.A. Woollam Company).
- the transmission data of the firms shown in the graph of Fig.42 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer.
- the mode used was nanometers, with a range of 300-3,300 nm.
- the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min.
- the baseline parameter was zero/baseline.
- the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.).
- a CEE IOOCB Spinner/Hotplate was used to apply Formulation 20 to wafers.
- the spin speed was 1,000- 5,000 rpm
- the acceleration was 4,500 rpm/sec
- the spin time was 360 seconds.
- a Canon PLA-501 F Parallel Light Mask Aligner with xenon lamp was used to cure the films.
- the output was 2.7 mJ-sec/cm 2 at 365 nm, the time was 12 minutes, and the total exposure dose was 2 J/cm 2 .
- the refractive index (n) and extinction coefficient (k) data were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J. A.
- the transmission data of the films shown in the graph of Fig.44 and expressed as a percentage, were obtained using a Varian Gary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer.
- the mode used was nanometers, with a range of 300-3,300 nm.
- the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nrn/min.
- the baseline parameter was ze ⁇ Vbaseline.
- the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.).
- a CEE IOOCB Spinner/Hotplate was used to apply formulation 21 to wafers. The spin speed was 1 ,000- 5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 60 seconds.
- a Canon PLA-50 IF Parallel Light Mask Aligner with xenon lamp was used to cure the films.
- the output was 2.7 mJ-sec/cm 2 at 365 nm, the time was 6 minutes, and the total exposure dose was 1 J/cm 2 .
- the refractive index (n) and extinction coefficient (Jc) data were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J.A. Woollam Company).
- the transmission data of the films shown in the graph of Fig.46 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer.
- the mode used was nanometers, with a range of 300-3,300 nm.
- the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min.
- the baseline parameter was zero/baseline.
Abstract
Novel compositions and methods of using those compositions to form high refractive index coatings are provided. The compositions preferably comprise both a reactive solvent and a high refractive index compound. Preferred reactive solvents include aromatic resins that are functionalized with one or more reactive groups (e.g., epoxides, vinyl ethers, oxetane), while preferred high refractive index compounds include aromatic epoxides, vinyl ethers, oxetanes, phenols, and thiols. An acid or crosslinking catalyst is preferably also included. The inventive compositions are stable under ambient conditions and can be applied to a substrate to form a layer and cured via light and/or heat application. The cured layers have high refractive indices and light transmissions.
Description
CURABLE HIGH REFRACTIVE INDEX RESINS FOR OPTOELECTRONIC APPLICATIONS
BACKGROUND OF THE INVENTION Related Applications
This application claims the priority benefit of U.S. Provisional Patent Application No. 60/614,017, filed September 28, 2004, incorporated by reference herein.
Field of the Invention The present invention is broadly concerned with novel compositions that can be formed into high refractive index layers. The compositions are useful for forming solid- state devices such as flat panel displays, optical sensors, integrated optical circuits, light- emitting diodes (LEDs), microlens arrays, and optical storage disks.
Description of the Prior Art
High refractive index coatings offer a improved performance in the operation of many optoelectronic devices. For example, the efficiency of LEDs is improved by applying a layer of high refractive index material between the device and the encapsulating material, thereby reducing the refractive index mismatch between the semiconductor substrate and the surrounding encapsulating plastic. A higher refractive index material also allows lenses to have a higher numerical aperture (NA), which leads to increased performance.
Many organic polymer systems offer high optical transparency and ease of processing, but seldom provide high refractive indices. Furthermore, most of the UV- curable resins currently available are based on free radical polymerization. This method, while allowing for rapid curing, is sensitive to the presence of oxygen. Optically clear epoxy resins, on the other hand, are mostly cured by thermal methods, have long cure times, or suffer from short pot lives.
A need exists for curable compositions that have high refractive indices and high optical transparency for use in optical and photonic applications.
SUMMARY OF THE INVENTION
The present invention overcomes these problems by providing novel compositions having high refractive indices and useful in the fabrication of optoelectronic components. The compositions broadly comprise a reactive solvent system (e.g., aromatic resin functionalized with one or more reactive groups such as epoxides, vinyl ethers, oxetanes) that dissolve a reactive high refractive index component such as aromatic epoxides, vinyl ethers, oxetanes, phenols, or thiols.
In more detail, the composition comprises a compound (I) having a formula selected from the group consisting of
where: each R is individually selected from the group consisting of hydrogen, alkyls
(preferably from about C1-C100, more preferably from about C1-C20, and even more preferably from about C1-C12), alkoxys (preferably from about C1-C100, more preferably from about C1-C50, and even more preferably from about C1-C12), cycloaliphatics (preferably from about C3-C100, more preferably from about C3-C12, and even more preferably from about
C5-C12), and aromatics (preferably from about C3-C100, more preferably from about C3-C50, and even more preferably from about C5-C12); each B is individually selected from the group consisting of -CO-, -COO-,
-CON-,-0-, -S-, -SO-, -SO2-, -CR2-, and -NR-; each Q is individually selected from the group consisting Of-CR2; each D is individually selected from the group consisting Of-VCRCR2, where V is selected from the group consisting of -O- and -S-; each Z is individually selected from the group consisting of
x is from about 0-6; and n is from about 0-100, preferably from about 1-50, and even more preferably from about 1-40.
Preferred Aromatic Moieties I include those selected from the group consisting of
Preferred Aromatic Moieties II include those selected from the group consisting of
Preferred Aromatic Moieties III include those selected from the group consisting of
In each of the structures of Aromatic Moieties I, Aromatic Moieties II, and Aromatic Moieties III above, the variables are defined as follows: each R' is individually selected from the group consisting of -C(CR"'3)2-, -CR'"2-, -SO2-, -S-, -SO- and -CO-, where each R'" is individually selected from the group consisting of hydrogen, alkyls (preferably from about C1-Ci00, more preferably from about C1-C20, and even more preferably from about C1- C12), alkoxys (preferably from about C1-C100, more preferably from about C1-C50, and even more preferably from about C1-C12), cycloaliphatics (preferably from about C3-C100, more preferably from about C3-C12, and even more preferably from about C5-C12), and aromatics (preferably from
about C3-Ci00, more preferably from about C3-C50, and even more preferably from about C5-C12); each R" is individually selected from the group consisting of -CR"',-, -SO2-, -SO-, -S-, -0-, -CO-, and -NR1"-, where each R"' is individually selected from the group consisting of hydrogen, alkyls (preferably from about C1-C100, more preferably from about C1-C20, and even more preferably from about C1- C12), alkoxys (preferably from about C1-C100, more preferably from about C1-C50, and even more preferably from about C1-C12), cycloaliphatics (preferably from about C3-C100, more preferably from about C3-C12, and even more preferably from about C5-C12), and aromatics (preferably from about C3-C100, more preferably from about C3-C50, and even more preferably from about C5-Cn),' each X is individually selected from the group consisting of the halogens (and most preferably Br and I); each m is 0-6 and more preferably from about 1-2; and each y is 0-6.
It will be understood that y can readily be selected by one of ordinary skill in the art, depending upon the value of m.
In preferred embodiments where the compound is acting as a reactive solvent. As used herein, a reactive solvent is one that reacts with the other compounds in the composition so as to be substantially (i.e., at least about 95% by weight, preferably at least about 99% by weight, and even more preferably about 100% by weight) consumed during the subsequent polymerization and crosslinking reactions. The reactive solvent also functions to dissolve the other ingredients in the composition to assist in homogenizing the composition.
In embodiments where the compound is acting as a high refractive index material, m will be at least 1. In order to achieve suitably high refractive indices, it is preferred that the X group be present in the compound to provide at least about 1% by weight X groups, more preferably from about 5-80% by weight X groups, and even more preferably from about 30-70% by weight X groups, based upon the total weight of the composition taken as 100% by weight.
In a particular preferred embodiment, the composition will comprise both the compound as a reactive solvent (i.e., without X groups) and as a high refractive index material (i.e., with X groups). It is preferred that the reactive solvent compound be present at levels of at least about 1% by weight, preferably from about 5-95% by weight, and even more preferably from about 10-50% by weight, based upon the total weight of the composition taken as 100% by weight. The high refractive index compound is preferably present at levels of at least about 1% by weight, preferably from about 5-95% by weight, and even more preferably from about 10-90% by weight, based upon the total weight of the composition taken as 100% by weight.
The composition also preferably comprises a crosslinking catalyst. Preferred crosslinking catalysts are selected from the group consisting of acids, photoacid generators (preferably cationic), photobases, thermal acid generators, thermal base generators, and mixtures thereof. Examples of particularly preferred crosslinking catalysts include those selected from the group consisting of substituted trifunctional sulfonium salts (preferably where at least one functional group is an aryl group), iodonium salts, disulfones, triazines, diazomethanes, and sulfonates. The crosslinking catalyst should be included at levels of from about 1-15% by weight, preferably from about 1-10% by weight, and even more preferably from about 1 -8% by weight, based upon the total weight of the reactive solvent and high refractive index material taken as 100% by weight.
In another embodiment, the composition preferably further comprises a compound selected from the group consisting of
where: each R" is individually selected from the group consisting of -CR'"2-, -SO2-, -SO-, -S-, -0-, -CO-, and -NR"'-, where each R'" is individually selected from the group consisting of hydrogen, alkyls (preferably from about C1-C100, more preferably from about C1-C20, and even more preferably from about C1- C12), alkoxys (preferably from about C1-Cj00, more preferably from about C1-C20, and even more preferably from about C1-C12), cycloaliphatics (preferably from about C3-C100, more preferably from about C3-C12, and even more preferably from about C5-C12), and aromatics (preferably from about C3-C100, more preferably from about C3-C50, and even more preferably from about C5-C12); each X is individually selected from the group consisting of the halogens (and most preferably Br and I); and each m is 0-6 and more preferably from about 1-2; and each y is 0-6.
It will be understood that y can readily be selected by one of ordinary skill in the art, depending upon the value of m. In a particularly preferred embodiment, the composition comprises very low levels of non-reactive solvents or diluents (e.g., PGME, PGMEA, propylene carbonate). Thus, the composition comprises less than about 5% by weight, preferably less than about 2% by weight, and even more preferably about 0% by weight non-reactive solvents or diluents, based upon the total weight of the composition taken as 100% by weight. It will be appreciated that other optional ingredients can be included in the inventive compositions as well. Examples of some optional ingredients include fillers, UV stabilizers, and surfactants.
The inventive compositions are formed by heating the reactive solvent compound(s) until it achieves a temperature of from about 20- 1000C, and more preferably from about 60-800C. The high refractive index compound(s) are then added and mixing
is continued until a substantially homogeneous mixture is obtained. The crosslinking catalyst and any other optional ingredients are then added and mixing is continued.
The compositions are applied to a substrate by any known method to form a coating layer or film thereon. Suitable coating techniques include dip coating, roller coating, inj ection molding, film casting, draw-down coating, or spray coating. A preferred method involves spin coating the composition onto the substrate at a rate of from about 500-5,000 rpm (preferably from about 1,000-4,000 rpm) for a time period of from about 30-480 seconds (preferably from about 60-300 seconds) to obtain uniform films. Substrates to which the coatings can be applied include those selected from the group consisting of silicon, silicon dioxide, silicon nitride, aluminum gallium arsenide, aluminum indium gallium phosphide, gallium nitride, gallium arsenide, indium gallium phosphide, indium gallium nitride, indium gallium arsenide, aluminum oxide (sapphire), glass, quartz, polycarbonates, polyesters, acrylics, polyurethanes, papers, ceramics, and metals (e.g., copper, aluminum, gold). The applied coatings are then cured by either baking or exposing to light having a wavelength effective for crosslinking the resin within the composition, depending upon the catalyst system utilized. If baked, the composition will be baked at temperatures of at least about 400C, and more preferably from about 50-1500C for a time period of at least about 5 seconds (preferably from about 10-60 seconds). Light exposure is the most preferred method of effecting curing of the composition because the most preferred inventive compositions are photocurable. In this curing method, light (e.g., at a wavelength of from about 100-1,000 nm (more preferably from about 240-400 nm) or at an exposure energy of from about 0.005-20 J/cm2 (more preferably from about 0.1-10 J/cm2) is used to generate the acid that catalyzes the polymerization and crosslinking reactions.
Cured coatings prepared according to the instant invention will have superior properties, and can be formulated to have thicknesses of from about 1-5,000 μm. For example, the cured coatings will have a refractive index of at least about 1.5, preferably at least about 1.56, and more preferably at least about 1.60, at wavelengths of from about 375-1 ,700 nm. Furthermore, cured coatings having a thickness of about 100 μm will have
a percent transmittance of at least about 80%, preferably at least about 90%, and even more preferably least about 95% at wavelengths of from about 375-1700 nm.
BRIEF DESCRIPTION OF THE DRAWINGS
Figure 1 is a graph depicting the n and k values for a cured layer formed from the composition of Example 1;
Fig. 2 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 1; Figs . 3 -3 d are graphs demonstrating the light stability at different energy levels of a cured layer formed from the composition of Example 1;
Figs.4-4c are graphs demonstrating the thermal stability over time of a cured layer formed from the composition of Example 1;
Fig. 5 is a graph depicting the n and k values for a cured layer formed from the composition of Example 2;
Fig. 6 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 2;
Figs. 7-7c are graphs demonstrating the light stability at different energy levels of a cured layer formed from the composition of Example 2; Figs. 8-8c are graphs demonstrating the thermal stability over time of a cured layer formed from the composition of Example 2;
Fig. 9 is a graph depicting the n and k values for a cured layer formed from the composition of Example 3;
Fig. 10 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 3;
Fig. 11 is a graph depicting the n and k values for a cured layer formed from the composition of Example 4;
Fig. 12 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 4; Fig. 13 is a graph depicting the n and k values for a cured layer formed from the composition of Example 5;
Fig. 14 is a graph showing the percent oflight transmission of a cured layer formed from the composition of Example 5;
Fig. 15 is a graph depicting the n and k values for a cured layer formed from the composition of Example 6; Fig. 16 is a graph showing the percent oflight transmission of a cured layer formed from the composition of Example 6;
Fig. 17 is a graph depicting the n and k values for a cured layer formed from the composition of Example 7;
Fig. 18 is a graph showing the percent oflight transmission of a cured layer formed from the composition of Example 7;
Fig. 19 is a graph depicting the n and k values for a cured layer formed from the composition of Example 8;
Fig.20 is a graph showing the percent oflight transmission of a cured layer formed from the composition of Example 8; Fig. 21 is a graph depicting the n and k values for a cured layer formed from the composition of Example 9;
Fig.22 is a graph showing the percent oflight transmission of a cured layer formed from the composition of Example 9;
Fig. 23 is a graph depicting the n and k values for a cured layer formed from the composition of Example 10;
Fig.24 is a graph showing the percent oflight transmission of a cured layer formed from the composition of Example 10;
Fig. 25 is a graph depicting the n and k values for a cured layer formed from the composition of Example 11; Fig.26 is a graph showing the percent oflight transmission of a cured layer formed from the composition of Example 11;
Fig. 27 is a graph depicting the n and k values for a cured layer formed from the composition of Example 12;
Fig.28 is a graph showing the percent oflight transmission of a cured layer formed from the composition of Example 12;
Fig. 29 is a graph depicting the n and k values for a cured layer formed from the composition of Example 13;
Fig. 30 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 13; Fig. 31 is a graph depicting the n and k values for a cured layer formed from the composition of Example 14;
Fig. 32 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 14;
Fig. 33 is a graph depicting the n and k values for a cured layer formed from the composition of Example 15;
Fig. 34 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 15;
Fig. 35 is a graph depicting the n and k values for a cured layer formed from the composition of Example 16; Fig.36 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 16;
Fig. 37 is a graph depicting the n and k values for a cured layer formed from the composition of Example 17;
Fig.38 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 17;
Fig. 39 is a graph depicting the n and k values for a cured layer formed from the composition of Example 18;
Fig.40 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 18; Fig. 41 is a graph depicting the n and k values for a cured layer formed from the composition of Example 19;
Fig.42 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 19;
Fig. 43 is a graph depicting the n and k values for a cured layer formed from the composition of Example 20;
Fig.44 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 20;
Fig. 45 is a graph depicting the n and k values for a cured layer formed from the composition of Example 21; and
Fig.46 is a graph showing the percent of light transmission of a cured layer formed from the composition of Example 21.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
EXAMPLES
The following examples set forth preferred methods in accordance with the invention. It is to be understood, however, that these examples are provided by way of illustration and nothing therein should be taken as a limitation upon the overall scope of the invention.
EXAMPLE l
A Curable High Refractive Index Resin Prepared with Aromatic Epoxides A. Preparation of Formulation 1 The following procedure was used to a prepare a curable high refractive index coating:
1. An oil bath was preheated to 80 ° C (oil temperature).
2. Approximately 50.00 grams of Dow D.E.R. 332 (Dow Plastics) were added to a 250-mL round-bottom flask. The amount used equaled the amount of Dow D.E.R. 560 (Dow Plastics) used in Step 4 below.
3. The round-bottom flask and its contents were heated to about 60-70 ° C while being stirred with a stir bar or mechanical stirrer.
4. Once the desired temperature was reached, Dow D.E.R. 560 (50.00 grams - an amount equal to the Dow D.E.R. 332 used in Step 2 above) was weighed out and slowly added to the stirring Dow D.E.R. 332.
5. The mixture was then stirred for 2 hours, or until both compounds were mixed.
6. Dow UVI-6976 (The Dow Chemical Company) was added in an amount of 2% by weight, based upon the combined weight of Dow D.E.R. 332 and Dow D.E.R. 550 taken as 100% by weight.
7. The mixture was allowed to cool slightly and then poured into an appropriate container.
B. Preparation of Films From Formulation 1
Using normal spin-coating techniques, Formulation 1 could be coated onto various types of wafers (silicon, quartz, glass, etc.). A typical spin-coating and UV-curing process is described in the following:
1. To spin coat the formulation onto a wafer, a CEE 1 OOCB Spinner/Hotplate (Brewer Science Inc.) was used. Spin speeds ranged from 1,000-5,000 rpm. Acceleration ranged from 500-20,000 rpm/sec. Spin times ranged from 90-360 seconds.
2. A Canon PLA-501F Parallel Light Mask Aligner with xenon lamp was used to cure the films. Output was 3.7 mJ-sec/cm2 at 365 run. Exposure times ranged from 10-12 minutes. Total exposure doses ranged from 1.2- 2.7 J/cm2.
Table 1 below shows representative film processing data specifically for these materials.
Table 1
The data in Table 2 were obtained through the analysis of the above films by use of a prism coupler (Metricon 2010).
Table 2
Refractive index (n) and extinction coefficient (k) data (see Fig. 1) were obtained using a variable angle spectroscopic ellipsometer (VASE, H-VASE, J.A. Woollam Company).
A Varian Gary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer was used to measure the light transmission quality of the films. The mode used was nanometers, with a range of 200 to 3,300 nm. For the scan controls, the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/rnin. The Y mode parameters were Y min = 0.00, and Y max = 100.00. The baseline parameter was zerc^aseline.
The graph of Fig. 2 shows the percent of light transmission (%T) of the films obtained using the parameters described above.
Light stability measurements were performed using a Canon PLA-501F Parallel Light Mask Aligner with xenon lamp with an average output of 2.45 mJ-sec/cm2 at 365 nm. The total exposure dose at 365 nm was 2.265 Joules. Film transmission, expressed as a percentage, is shown in Fig. 3.
Thermal stability of the film was investigated using a Blue M Electric Company Convection Oven, Model ESP-400BC-4, and subjecting the cured firms to a temperature of 100°C for 20 days. Film transmission, expressed as a percentage, is shown in Fig. 4.
EXAMPLE 2
Curable High Refractive Index Resin Prepared with Epoxides and a Brominated Epoxy Novolac Resin
A. Preparation of Formulation 2 The following procedure was used to prepare a curable high refractive index coating:
1. An oil bath was preheated to 800C (oil temperature).
2. Approximately 40.00 grams of Dow D.E.R. 332 were added to a 250-mL round- bottom flask. 3. The flask and its contents were heated to about 60-70 ° C while being stirred with a stir bar or mechanical stirrer.
4. Once the desired temperature was reached, 60.00 grams of BREN 304 (Nippon Kayaku Company, Ltd.) were weighed out and slowly added to the stirring Dow D.E.R. 332. 5. The contents of the flask were stirred for 2 hours or until both compounds were mixed.
6. Dow UVI-6976 (The Dow Chemical Company) was added in an amount of 2% by weight, based upon the combined weight of the Dow D.E.R. 332 and (Nippon Kayaku Company, Ltd.) taken as 100% by weight. 7. The contents of the flask were then allowed to mix for 30-45 minutes.
8. The mixture was allowed to cool slightly and then poured into an appropriate container.
B. Preparation of Films From Formulation 2 Using normal spin-coating and UV-curing techniques, the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.). A CEE IOOCB Spinner/Hotplate was used to apply Formulation 2 to wafers. The spin speed was 1,000- 5,000 rpm, acceleration was 4,500 rpm/seα, and the spin time was 420 seconds.
To cure the films, a Canon PLA-501F Parallel Light Mask Aligner with xenon lamp was used. Output was 2.7 mJ-sec/cm2 at 365 nm. Time was 10-12 minutes. Total exposure doses ranged from 1.2- 2.7 J/cm2
Representative film processing data for these materials are shown in Table 3.
Table 3
The data in Table 4 were obtained through the analysis of the above films by using a prism coupler (Metricon 2010).
Table 4
The refractive index (n) and extinction coefficient (k) data (see Fig. 5) were obtained using a variable angle spectroscopic ellipsometer (VASE, H-VASE, J.A.
Woollam Company).
The transmission data of the films, shown in the graph of Fig. 6 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer. The mode used was nanometers, with a range of 200-3,300 nm. For the scan controls, the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min. The Y mode parameters were Y min = 0.00, and Y max = 100.00. The baseline parameter was zero/baseline.
Light stability measurements were performed using a Canon PLA-501F Parallel Light Mask Aligner with xenon lamp, with an average output of 2.45 mJ-sec at 365 nm
and a total exposure dose at 365 run of 2265 Joules. The film transmission, expressed as a percentage, is shown in Fig. 7.
The thermal stability of the film was investigated using a Blue M Electric Company Convection Oven, Model ESP-400BC-4, and subjecting the cured films to a temperature of 100 °C for 6 days. The film transmission, expressed as a percentage, is shown in Fig. 8.
EXAMPLE 3
A Curable High Refractive Index Resin Prepared with Aromatic Epoxides and an Aromatic Epoxy Diluent
A. Preparation of Formulation 3
The following procedure was used to prepare a curable high refractive index coating:
1. An oil bath was preheated to 80 ° C (oil temperature). 2. Approximately 43.93 grams ofDowD.E.R.332and 10.04gERISYS GE-IO (CVC
Chemical Specialties Inc.) were added to a 250-mL round-bottom flask.
3. The flask and its contents were heated to about 60-70 ° C while being stirred with a stir bar or mechanical stirrer.
4. Once the desired temperature was reached, 44.00 grams of Dow D.E.R. 560 were slowly added to the stirring Dow D.E.R. 332 and ERISYS GE-10 mixture.
5. The contents of the flask were stirred for 2 hours or until all compounds were mixed.
6. Dow UVI-6976 (The Dow Chemical Company) was added in an amount of 2% by weight, based upon the combined weight of the ingredients already added taken as 100% by weight.
7. The contents of the flask were then allowed to mix for 2.5 hours.
8. The mixture was allowed to cool slightly and then poured into an appropriate container.
B. Preparation of Films From Formulation 3
Using normal spin-coating and UV-curing techniques, the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.). A CEE IOOCB Spinner/Hotplate was used to apply Formulation 3 to wafers. Spin speed was 1,000-5000 rpm, acceleration was 4,500 rpm/sec, and spin time was 60 seconds.
To cure the films, a Canon PLA-501F Parallel Light Mask Aligner with xenon lamp was used. The output was 2.7 mJ-sec/cm2 at 365 nm, the time was 12 minutes, and the total exposure dose was 2.0 J/cm2.
Representative film processing data for these materials are shown in Table 5.
Table 5
The data of Table 6 were obtained through the analysis of the above films by using a prism coupler (Metricon 2010).
Table 6
The refractive index (n) and extinction coefficient (k) data (see Fig. 9) were obtained using a variable angle spectroscopic ellipsometer (VASE, H-VASE, J.A. Woollam Company).
The transmission data of the films, shown in the graph of Fig. 10 and expressed as a percentage, were obtained using a Varian Gary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer. The mode used was nanometers, with a range of 300-3,300 nm. For the scan controls, the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min. The Y mode parameters were Y min = 0.00, and
Y max = 100.00. The baseline parameter was zero/baseline.
EXAMPLE 4
A Curable High Refractive Index Resin Prepared with Aromatic Epoxides and an Aromatic Vinyl Ether Diluent
A. Preparation of Formulation 4
The following procedure was used to prepare a curable high refractive index coating:
1. An oil bath was preheated to 80°C (oil temperature). 2. Approximately 44.98 grams of Dow D.E.R. 332 were added to a 250-mL round- bottom flask.
3. The flask and its contents were heated to about 60-700C while being stirred with a stir bar or mechanical stirrer.
4. Once the desired temperature was reached, 44.98 grams of Dow D.E.R. 560 were slowly added to the stirring Dow D.E.R. 332.
5. The contents of the flask were stirred for 1 hour until both compounds were mixed.
6. Next, 10.01 grams VECTOMER 4010 (available from Morflex) were added dropwise.
7. The mixture was stirred for 30 minutes. 8. Dow UVI-6976 (The Dow Chemical Company) was added in an amount of 2% by weight, based upon the combined weight of the ingredients already added taken as 100% by weight.
9. The contents of the flask were mixed for 60 minutes.
10. The mixture was allowed to cool slightly and then poured into an appropriate container.
B. Preparation of Films From Formulation 4
Using normal spin-coating and UV-curing techniques, the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.). A CEE IOOCB Spinner/Hotplate was used to apply Formulation 4 to wafers. The spin speed was 1,000 - 5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 60 seconds. The films were then baked for 6 sec at 1120C.
A Canon PLA-5 OIF Parallel Light Mask Aligner with xenon lamp was used to cure the films. The output was 2.7 mJ-sec/cm2 at 365 nm, the time was 9 minutes, and the total exposure dose was 1.5 J/cm2.
Representative film processing data for these materials are in Table 7.
Table 7
The data below were obtained through the analysis of the above films by using a prism coupler (Metricon 2010).
Table 8
The refractive index (n) and extinction coefficient (k) data (see Fig. 11) were obtained using a variable angle spectroscopic ellipsometer (VASE, H-VASE, J.A. Woollam Company).
The transmission data of the films, shown in the graph of Fig. 12 and expressed as a percentage, were obtained using a Varian Gary 500 Scan UV-Vis-NIR Dual Beam
Spectrophotometer. The mode used was nanometers, with a range of 300-3,300 nm. For the scan controls, the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min. The Y mode parameters were Y min = 0.00, and Y max = 100.00. The baseline parameter was zero/baseline.
EXAMPLE 5 A Curable High Refractive Index Resin Prepared with Aromatic Epoxides,
Aromatic Vinyl Ethers and Aromatic Epoxy Diluents A. Preparation of Formulation 5 The following procedure was used to prepare a curable high refractive index coating:
1. An oil bath was preheated to 800C (oil temperature).
2. Approximately 44.10 grams of Dow D.E.R. 332 and 5.00 grams ERISYS GE-10 (CVC Chemical Specialties) were added to a 250-mL round-bottom flask. 3. The flask and its contents were heated to about 60-70° C while being stirred with a stir bar or mechanical stirrer.
4. Once the desired temperature was reached, 44.03 grams of Dow D.E.R. 560 were slowly added to the stirring Dow D.E.R. 332.
5. The contents of the flask were stirred for 1.5 hours until both compounds were mixed.
6. Next, 5.00 grams of Morflex Vectomer 4010 were added dropwise.
7. Dow UVI-6976 (The Dow Chemical Company) was added in an amount of 2% by weight, based upon the combined weight of the ingredients already added taken as 100% by weight. 8. The mixture was stirred for 3 hours.
9. The mixture was allowed to cool slightly and then poured into an appropriate container.
B. Preparation of Films From Formulation 5
Using normal spin-coating and UV-curing techniques, the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.). A CEE IOOCB Spinner/Hotplate was used to apply Formulation 5 to wafers. The spin speed was 1,000- 5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 60 seconds.
A Canon PLA-50 IF Parallel Light Mask Aligner with xenon lamp was used to cure the firms. The output was 2.7 mJ-sec/cm2 at 365 nm, the time was 12 minutes, and the total exposure dose was 2.0 J/cm2.
Representative film processing data for these materials are shown in Table 9.
Table 9
The data of Table 10 were obtained through the analysis of the above firms by using a prism coupler (Metricon 2010).
Table 10
The refractive index (n) and extinction coefficient (k) data (see Fig. 13) were obtained using a variable angle spectroscopic ellipsometer (VASE, H-VASE, J.A. Woollam Company).
The transmission data of the films, shown in the graph of Fig. 14 and expressed as a percentage, were obtained using a Varian Gary 500 Scan UV-Vis-NIR Dual Beam
Spectrophotometer. The mode used was nanometers, with a range of 300-3,300 nm. For the scan controls, the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min. The Y mode parameters were Y min = 0.00, and Y max = 100.00. The baseline parameter was zero/baseline.
EXAMPLE 6 A Curable High Refractive Index Resin Prepared with Aromatic
Epoxides and a Brominated Aromatic Epoxy Diluent A. Preparation of Formulation 6 The following procedure was used to prepare a curable high refractive index coating:
1. An oil bath was preheated to 80 ° C (oil temperature).
2. Approximately 44.0 grams of Dow D.E.R. 332 were added to a 250-mL round- bottom flask. 3. The flask and its contents were heated to about 60-70 ° C while being stirred with a stir bar or mechanical stirrer.
4. Once the desired temperature was reached, 44.0 grams of Dow D.E.R. 560 were slowly added to the stirring Dow D.E.R. 332.
5. The contents of the flask were stirred for 2 hours until both compounds were mixed.
6. Next, 10.0 grams of Nagase ChemTex DENACOL EX-147 were added dropwise.
7. Dow UVI-6976 (The Dow" Chemical Company) was added in the amount of 2% by weight, based upon the combined weight of the ingredients already added taken as 100% by weight. 8. The mixture was stirred for 3 hours.
9. The mixture was allowed to cool slightly and then poured into an appropriate container.
B. Preparation of Films From Formulation 6
Using normal spin-coating and UV-curing techniques, the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.). A CEE IOOCB Spinner/Hotplate was used to apply Formulation 6 to wafers. The Spin speed was 1,000 - 5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 360 seconds.
A Canon PLA-50 IF Parallel Light Mask Aligner with xenon lamp was used to cure the films. The output was 2.7 mJ-sec/cm2 at 365 nm, the time was 12 minutes, and the total exposure dose was 2.0 J/cm2.
Representative film processing data for these materials are shown in Table 11.
Table 11
The data of Table 12 were obtained through the analysis of the above films by using a prism coupler (Metricon 2010).
Table 12
The refractive index (n) and extinction coefficient (k) data (see Fig. 15) were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J.A. Woollam Company).
The transmission data of the films, shown in the graph of Fig. 16 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam
Spectrophotometer. The mode used was nanometers, with a range of 300-3,300 nm. For the scan controls, the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nrn/min. The Y mode parameters were Y min = 0.00, and Y max = 100.00. The baseline parameter was zero/baseline.
EXAMPLE 7
A Curable High Refractive Index Resin Prepared with Aromatic Epoxides, an Aromatic Vinyl Ether and an Aromatic Oxetane Diluent A. Preparation of Formulation 7 The following procedure was used to prepare a curable high refractive index coating:
1. An oil bath was preheated to 80° C (oil temperature).
2. Approximately 44.03 grams of Dow D.E.R. 332 were added to a 250-mL round- bottom flask. 3. The flask and its contents were heated to about 60-70 ° C while being stirred with a stir bar or mechanical stirrer.
4. Once the desired temperature was reached, 44.06 grams of Dow D.E.R. 560 were slowly added to the stirring Dow D.E.R. 332.
5. The contents of the flask were stirred for 2 hours until both compounds were mixed.
6. Next, 10.00 grams Toagosei Co., Ltd. OXT-121 were added dropwise.
7. Dow UVI-6976 (The Dow Chemical Company) was added in the amount of 2% by weight, based upon the combined weight of the ingredients already added taken as 100% by weight. 8. The mixture was stirred for 3 hours.
9. The mixture was allowed to cool slightly and then poured into an appropriate
container.
B. Preparation of Films From Formulation 7
Using normal spin-coating and UV-curing techniques, the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.). A CEE IOOCB Spinner/Hotplate was used to apply Foπnulation 7 to wafers. Spin speed was 1,000 - 5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 360 seconds.
A Canon PLA-501 F Parallel Light Mask Aligner with xenon lamp was used to cure the films. The output was 2.7 mJ-sec/cm2 at 365 nm, the time was 12 minutes, and the total exposure dose was 2.0 J/cm2.
Representative film processing data for these materials are shown in Table 13.
Table 13
The data of Table 14 were obtained through the analysis of the above films by using a prism coupler (Metricon 2010).
Table 14
The refractive index (n) and extinction coefficient (k) data (see Fig. 17) were
obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J.A. Woollam Company).
The transmission data of the films, shown in the graph of Fig. 18 and expressed as a percentage, were obtained using a Varian Gary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer. The mode used was nanometers, with a range of 300-3,300 nm. For the scan controls, the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min. The Y mode parameters were Y min = 0.00, and Y max = 100.00. The baseline parameter was zero/baseline.
EXAMPLE 8
A Curable High Refractive Index Resin Prepared with Epoxy Novolac Resin
A. Preparation of Formulation 8
The following procedure was used to prepare a curable high refractive index coating:
1. An oil bath was preheated to 80 ° C (oil temperature) .
2. Approximately 117.93 grams of Dow D.E.N.431 were added to a 250-tnL round- bottom flask.
3. The flask and its contents were heated to about 60-700C while being stirred with a stir bar or mechanical stirrer.
4. Dow UVI-6976 (The Dow Chemical Company) was added in an amount of 2% by weight, based upon the combined weight of the ingredients already added taken as 100% by weight.
5. The mixture was stirred for 3 hours. 6. The mixture was allowed to cool slightly and then poured into an appropriate container.
B. Preparation of Films From Formulation 8
Using normal spin-coating and UV-curing techniques, the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.). A CEE IOOCB
Spinner/Hotplate was used to apply Formulation 8 to wafers. The spin speed was 1,000- 5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 60 seconds.
A Canon PLA-50 IF Parallel Light Mask Aligner with xenon lamp was used to cure the films. The output was 2.7 mJ-sec/cm2 at 365 nm, the time was 12 minutes, and the total exposure doses was 2.0 J/cm2.
Representative film processing data for these materials are shown in Table 15.
Table 15
The data shown in Table 16 were obtained through the analysis of the above films by using a prism coupler (Metricon 2010).
Table 16
The refractive index (n) and extinction coefficient (k) data (see Fig. 19) were obtained using a variable angle spectroscopic ellipsometer (VASE, H-VASE, J.A.
Woollam Company).
The transmission data of the films, shown in the graph of Fig.20 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer. The mode used was nanometers, with a range of 300-3,300 nm. For
the scan controls, the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min. The Y mode parameters were Y min = 0.00, and Y max = 100.00. The baseline parameter was zero/baseline.
EXAMPLE 9
A Curable High Refractive Index Resin Prepared with Epoxy Novolac Resin and an Aromatic Epoxy Diluent
A. Preparation of Formulation 9
The following procedure was used to prepare a curable high refractive index coating:
1. First, 89.03 grams Dow D.E.N. 431, 9.03 grams ERISYS GE-10 (CVC Chemical Specialties), and 1.99 grams Dow UVI-6976 were measured into a 125-mL, brown Nalgene bottle.
2. The components were combined on a mixing wheel for 72 hours at 50 rpm.
B. Preparation of Films From Formulation 9
Using normal spin-coating and UV-curing techniques, the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.). A CEE IOOCB Spinner/Hotplate was used to apply Formulation 9 to wafers. The spin speed was 1,000- 5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 360 seconds.
A Canon PLA-50 IF Parallel Light Mask Aligner with xenon lamp was used to cure the films. The output was 2.7 mJ-sec/cm2 at 365 nm, the time was 12 minutes, and the total exposure dose was 2.0 J/cm2.
Representative film processing data for these materials are shown in Table 17.
Table 17
The data of Table 18 were obtained through the analysis of the above films by using a prism coupler (Metricon 2010).
Table 18
The refractive index (n) and extinction coefficient (k) data (see Fig. 21) were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J.A. Woollam Company).
The transmission data of the films, shown in the graph of Fig. 22 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer. The mode used was nanometers, with a range of 300-3,300 nm. For the scan controls, the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min. The Y mode parameters were Y min = 0.00, and Y max = 100.00. The baseline parameter was zero/baseline.
EXAMPLE 10
A Curable High Refractive Index Resin Prepared with Epoxy Novolac Resin and an Aromatic Vinyl Ether Diluent A. Preparation of Formulation 10
The following procedure was used to prepare a curable high refractive index coating:
1. First, 60.86 grams Dow D.E.N.431 , 6.16 grams VECTOMER 4010 (Morflex), and 1.37 grams Dow UVI-6976 were measured into a 125-mL, brown Nalgene bottle.
2. The components were combined on a mixing wheel for 72 hours at 50 rpm.
B. Preparation of Films From Formulation 10
Using normal spin-coating and UV-curing techniques, the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.). A CEE IOOCB Spinner/Hotplate was used to apply Formulation 10 to wafers. Spin speed was 1,000- 5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 360 seconds.
A Canon PLA-5 OIF Parallel Light Mask Aligner with xenon lamp was used to cure the films. The output was 2.7 mJ-sec/cm2 at 365 nm, the time was 7.5 minutes, and the total exposure dose was 1.2 J/cm2.
Representative film processing data for these materials are shown Table 19.
Table 19
The data from Table 20 were obtained through the analysis of the above films by using a prism coupler (Metricon 2010).
Table 20
The refractive index (n) and extinction coefficient (k) data (see Fig. 23) were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J.A. Woollam Company).
The transmission data of the films, shown in the graph of Fig. 24 and expressed as a percentage, were obtained using a Varian Gary 500 Scan UV-Vis-NIR Dual Beam
Spectrophotometer. The mode used was nanometers, with a range of 300-3,300 nm. For the scan controls, the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min. The Y mode parameters were Y min = 0.00, and Y max = 100.00. The baseline parameter was zero/baseline.
EXAMPLE I l
A Curable High Refractive Index Resin Prepared with Epoxy Novolac Resin and an Aromatic Oxetane Diluent A. Preparation of Formulation 11 The following procedure was used to prepare a curable high refractive index coating:
1. An oil bath was preheated to 80 ° C (oil temperature).
2. Approximately 88.74 grams of Dow D.E.N. 431 and 8.96 grams OXT-121 (Toagosei Co., Ltd.) were added to a 250-mL round-bottom flask. 3. The flask and its contents were heated to about 60-70° C while being stirred with a stir bar or mechanical stirrer.
4. The mixture was stirred for 40 minutes.
5. Dow UVI-6976 (The Dow Chemical Company) was added in an amount of 2% by weight, based upon the combined weight of the ingredients already added taken as 100% by weight.
6. The mixture was stirred for 50 minutes.
7. The mixture was allowed to cool slightly and then poured into an appropriate container.
B. Preparation of Films From Formulation 11
Using normal spin-coating and UV-curing techniques, the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.). A CEE IOOCB Spinner/Hotplate was used to apply Formulation 11 to wafers. The spin speed was 1,000- 5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 60 seconds.
A Canon PLA-5 OIF Parallel Light Mask Aligner with xenon lamp was used to cure the films. The output was 2.7 mJ-sec/cm2 at 365 nm, the time was 7.5 minutes, and the total exposure dose was 1.2 J/cm2.
Representative film processing data for these materials are shown in Table 21.
Table 21
The data of Table 22 were obtained through the analysis of the above films by using a prism coupler (Metricon 2010).
Table 22
The refractive index (n) and extinction coefficient (k) data (see Fig. 25) were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J.A. Woollam Company).
The transmission data of the films, shown in the graph of Fig. 26 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer. The mode used was nanometers, with a range of 300-3300 nm. For the scan controls, the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min. The Y mode parameters were Y min = 0.00, and
Y max = 100.00. The baseline parameter was zero/baseline.
EXAMPLE 12
A Curable High Refractive Index Resin Prepared with Epoxy Novolac Resin and a Brominated Aromatic Epoxy Diluent
A. Preparation of Formulation 12
The following procedure was used to prepare a curable high refractive index coating:
1. An oil bath was preheated to 80 ° C (oil temperature). 2. Approximately 89.13 grams ofDow D.E.N. 431 and 9.01 grams DENACOL EX-
147 (Nagase ChemTex) were added to a 250-mL round-bottom flask.
3. The flask and its contents were heated to about 60-700C while being stirred with a stir bar or mechanical stirrer.
4. The mixture was stirred for 2 hours. 5. Dow UVI-6976 (The Dow Chemical Company) was added in the amount of 2% by weight, based upon the combined weight of the ingredients already added taken as 100% by weight.
6. The mixture was stirred for 3 hours.
7. The mixture was allowed to cool slightly and then poured into an appropriate container.
B. Preparation of Films From Formulation 12
Using normal spin-coating and UV-curing techniques, the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.). A CEE IOOCB Spinner/Hotplate was used to apply Formulation 12 to wafers. The spin speed was 1 ,000-
5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 360 seconds.
A Canon PLA-50 IF Parallel Light Mask Aligner with xenon lamp was used to cure the films. The output was 2.7 mJ-sec/cm2 at 365 nm, and the time was 10 minutes, and the total exposure dose was 1.6 J/cm2.
Representative film processing data for these materials are shown in Table 23.
Table 23
The data of Table 24 were obtained through the analysis of the above films by using a prism coupler (Metricon 2010).
Table 24
The refractive index (n) and extinction coefficient (k) data (see Fig. 27) were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J.A. Woollam Company). The transmission data of the films, shown in the graph of Fig.28 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer. The mode used was nanometers, with a range of 300-3,300 nm. For the scan controls, the average time was 0.1 second, the data interval was 1.0 nm, and the
scan rate was 600 nm/min. The Y mode parameters were Y min = 0.00, and Y max = 100.00. The baseline parameter was zero/baseline.
EXAMPLE 13
A Curable High Refractive Index Resin Prepared with a Brominated Epoxy Resin A. Preparation of Formulation 13
The following procedure was used to prepare a curable high refractive index coating:
1. First, 94.99 grams of DENACOL EX-147 (Nagase ChemTex ) and 4.99 grams of Dow UVI-6976 were measured into a 125-mL, brown Nalgene bottle.
2. The components were combined on a mixing wheel for 24 hours at 50 rpm.
B. Preparation of Films From Formulation 10
Using normal spin-coating and UV-curing techniques, the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.). A CEE IOOCB Spinner/Hotplate was used to apply Formulation 13 to wafers . The spin speed was 1,000- 5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 60 seconds.
A CanonPLA-50 IF Parallel Light Mask Aligner with xenon lamp was used to cure the films. The output was 2.7 mJ-sec/cm2 at 365 nm, the time was 12 minutes, and the total exposure doses was 2.0 J/cm2.
Representative film processing data for these materials are shown in Table 25.
Table 25
The data of Table 26 were obtained through the analysis of the above films by using a prism coupler (Metricon 2010).
Table 26
The refractive index (n) and extinction coefficient (k) data (see Fig. 29) were obtained using a variable angle spectroscopic ellipsometer (VASE, H-VASE, J. A.
Woollam Company).
The transmission data of the films, shown in the graph of Fig. 30 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer. The mode used was nanometers, with a range of 300-3,300 nm. For the scan controls, the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min. The Y mode parameters were Y min = 0.00, and Y max = 100.00. The baseline parameter was zero/baseline.
EXAMPLE 14 A Curable High Refractive Index Resin Prepared with a
Brominated Epoxy Resin and an Aromatic Vinyl Ether Diluent A. Preparation of Formulation 14
The following procedure was used to prepare a curable high refractive index coating: 1. First, 89.07 grams of DENACOL EX-147 (Nagase ChemTex), 9.00 grams of
VECTOMER 4010 (Morflex), and 2.03 grams Dow UVI-6976 were measured into a 125-mL, brown Nalgene bottle. 2. The components were combined on a mixing wheel for 24 hours at 50 rpm.
B. Preparation of Films From Formulation 14
Using noπnal spin-coating and UV-curing techniques, the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.). A CEE IOOCB Spinner/Hotplate was used to apply formulation 14 to wafers. The spin speed was 1,000- 5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 60 seconds.
A Canon PLA-501 F Parallel Light Mask Aligner with xenon lamp was used to cure the films. The output was 2.7 mJ-sec/cm2 at 365 nm, the time was 37 minutes, and the total exposure dose was 6.03 J/cm2.
Representative film processing data for these materials are shown in Table 27.
Table 27
The data of Table 28 were obtained through the analysis of the above films by using a prism coupler (Metricon 2010).
Table 28
The refractive index (n) and extinction coefficient (k) data (see Fig. 31) were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J.A. Woollam Company).
The transmission data of the films, shown in the graph of Fig. 32 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer. The mode used was nanometers, with a range of 300-3,300 nm. For the scan controls, the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min. The Y mode parameters were Y min = 0.00, and
Y max = 100.00. The baseline parameter was zero/baseline.
EXAMPLE 15
A Curable High Refractive Index Resin Prepared with a Brominated Epoxy Resin and an Aromatic Oxetane Diluent
A. Preparation of Formulation 15
The following procedure was used to prepare a curable high refractive index coating:
1. First, 89.01 grams DENACOL EX-147 (Nagase ChemTex), 9.04 grams OXT-121 (Toagosei Co., Ltd.), and 2.02 grams Dow UVI-6976 were measured into a 125- mL, brown Nalgene bottle.
2. The components were combined on a mixing wheel for 72 hours at 50 rpm.
B. Preparation of Films From Formulation 15 Using normal spin-coating and UV-curing techniques, the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.). A CEE IOOCB Spinner/Hotplate was used to apply Formulation 15 to wafers. The spin speed was 1,000- 5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 60 seconds.
A Canon PLA-5 OIF Parallel Light Mask Aligner with xenon lamp was used to cure the films. The output was 2.7 mJ-sec/cm2 at 365 nm, the time was 12 minutes, and the total exposure dose was 2.0 J/cm2.
Representative film processing data for these materials are shown in Table 29.
Table 29
The data of Table 30 were obtained through the analysis of the above films by using a prism coupler (Metricon 2010).
Table 30
The refractive index (n) and extinction coefficient (k) data of Fig.33 were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J.A. Woollam Company). The transmission data of the films, shown in the graph of Fig. 34 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer. The mode used was nanometers, with a range of 300-3300 nm. For the scan controls, the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min. The Y mode parameters were Y min = 0.00, and Y max = 100.00. The baseline parameter was zero/baseline.
EXAMPLE 16
A Curable High Refractive Index Resin Prepared with a Brominated Epoxy Resin and a Brominated Epoxy Novolac
A. Preparation of Formulation 16 The following procedure was used to prepare a curable high refractive index coating:
1. First, 89.02 grams of DENACOL EX-147 (Nagase ChemTex), 9.03 grams BREN 304 (Nippon Kayaku Company, Ltd.), and 2.01 grams Dow UVI-6976 were measured into a 125-mL, brown Nalgene bottle. 2. The components were combined on a mixing wheel for 72 hours at 50 rpm.
B. Preparation of Films From Formulation 16
Using normal spin-coating and UV-curing techniques, the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.). A CEE IOOCB Spinner/Hotplate was used to apply Formulation 16 to wafers. The spin speed was 1 ,000-
5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 60 seconds.
A Canon PLA-50 IF Parallel Light Mask Aligner with xenon lamp was used to cure the films. The output was 2.7 mJ-sec/cm2 at 365 nm, the time was 14.5 minutes, and the total exposure dose was 2.3 J/cm2. Representative film processing data for these materials are shown in Table 31.
Table 31
The data of Table 32 were obtained through the analysis of the above films by using a prism coupler (Metricon 2010).
Table 32
The refractive index (n) and extinction coefficient (k) data (see Fig. 35) were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J. A.
Woollam Company).
The transmission data of the films, shown in the graph of Fig. 36 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer. The mode used was nanometers, with a range of 300-3,300 nm. For the scan controls, the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min. The Y mode parameters were Y min = 0.00, and Y max = 100.00. The baseline parameter was zero/baseline.
EXAMPLE 17 A Curable High Refractive Index Resin Prepared with a Brominated Epoxy Resin and an Epoxy Novolac A. Preparation of Formulation 17
The following procedure was used to prepare a curable high refractive index coating: 1. First, 89.00 grams of DENACOL EX- 147 (Nagase ChemTex), 9.00 grams Dow
D.E.N.431 , and 2.02 grams Dow UVI-6976 were measured into a 125-mL, brown Nalgene bottle. 2. The components were combined on a mixing wheel for 72 hours at 50 rpm.
B. Preparation of Films From Formulation 17
Using normal spin-coating and UV-curing techniques, the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.). A CEE IOOCB Spinner/Hotplate was used to apply Formulation 17 to wafers. The spin speed was 1 ,000-
5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 60 seconds.
A Canon PLA-5 OIF Parallel Light Mask Aligner with xenon lamp was used to cure the films. The output was 2.7 mJ-sec/cm2 at 365 run, the time was 12 minutes, and the total exposure dose was 1.9 J/cm2.
Representative film processing data for these materials are shown in Table 33.
Table 33
The data of Table 34 were obtained through the analysis of the above films by using a prism coupler (Metricon 2010).
Table 34
The refractive index (n) and extinction coefficient (k) data (see Fig. 37) were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J.A. Woollam Company).
The transmission data of the films, shown in the graph of Fig. 38 and expressed as a percentage, were obtained using a Varian Gary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer. The mode used was nanometers, with a range of 300-3,300 nm. For the scan controls, the average time was 0.1 second, the data interval was 1.0 nm, and the
scan rate was 600 nm/min. The Y mode parameters were Y min = 0.00, and Y max = 100.00. The baseline parameter was zero/baseline.
EXAMPLE 18
A Curable High Refractive Index Resin Prepared with a Brominated Epoxy Resin and a Brominated Epoxy Resin A. Preparation of Formulation 18
The following procedure was used to prepare a curable high refractive index coating:
1. First, 89.01 grams DENACOL EX-147 (Nagase ChemTex), 9.00 grams Dow D.E.R. 560, and 2.01 grams Dow UVI-6976 were measured into a 125-mL, brown Nalgene bottle.
2. The components were combined on a mixing wheel for 72 hours at 50 rpm.
B. Preparation of Films From Formulation 18
Using normal spin-coating and UV-curing techniques, the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.). A CEE IOOCB Spinner/Hotplate was used to apply Formulation 18 to wafers. Spin speed was 1,000- 5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 60 seconds. A Canon PLA-501 F Parallel Light Mask Aligner with xenon lamp was used to cure the films. The output was 2.7 mJ-sec/cm2 at 365 nm, the time was 14 minutes, and the total exposure doses was 2.3 J/cm2.
Representative film processing data for these materials are shown in Table 35.
Table 35
The data of Table 36 were obtained through the analysis of the above films by using a prism coupler (Metricon 2010).
Table 36
The refractive index (n) and extinction coefficient (k) data (see Fig. 39) were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J.A. Woollam Company) .
The transmission data of the films, shown in the graph of Fig.40 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer. The mode used was nanometers, with a range of 300-3,300 nm. For the scan controls, the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min. The Y mode parameters were Y min = 0.00, and
Y max = 100.00. The baseline parameter was zero/baseline.
EXAMPLE 19
A Curable High Refractive Index Resin Prepared with a Brominated Epoxy Resin and an Aromatic Epoxy Diluent
A. Preparation of Formulation 19
The following procedure was used to prepare a curable high refractive index coating:
1. An oil bath was preheated to 80°C (oil temperature). 2. Approximately 29.13 grams of ERISYS GE-10 (CVC Chemical Specialties) were added to a 250-mL, round-bottom flask.
3. The flask and its contents were heated to about 60-70 ° C while being stirred with a stir bar or mechanical stirrer.
4. Over a period of 2 hours, 69.00 grams Dow D.E.R.560 were added to the ERISYS GE-IO.
5. Dow UVI-6976 (The Dow Chemical Company) was added in an amount of 2% by weight, based upon the combined weight of the ingredients already added taken as 100% by weight.
6. The mixture was stirred for 3 hours.
7. The mixture was allowed to cool slightly and then poured into an appropriate container.
B. Preparation of Films From Formulation 19
Using normal spin-coating and UV-curing techniques, the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.). A CEE IOOCB Spinner/Hotplate was used to apply Formulation 19 to wafers. The spin speed was 1 ,000- 5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 60 seconds. A Canon PLA-501 F Parallel Light Mask Aligner with xenon lamp was used to cure the films. The output was 2.7 mJ-sec/cnr at 365 nm, the time was 12 minutes, and the total exposure doses was 2 J/cm2.
Representative film processing data for these materials are shown in Table 37.
Table 37
The data of Table 38 were obtained through the analysis of the above films by using a prism coupler (Metricon 2010).
Table 38
The refractive index (n) and extinction coefficient (k) data (see Fig. 41) were obtained using a variable angle spectroscopic ellipsometer (VASE, H-VASE, J.A. Woollam Company).
The transmission data of the firms, shown in the graph of Fig.42 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer. The mode used was nanometers, with a range of 300-3,300 nm. For the scan controls, the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min. The Y mode parameters were Y min = 0.00, and Y max = 100.00. The baseline parameter was zero/baseline.
EXAMPLE 20
A Curable High Refractive Index Resin Prepared with an Epoxy Novolac Resin and a Brominated Epoxy Diluent
A. Preparation of Formulation 20
The following procedure was used to prepare a curable high refractive index coating:
1. First, 79.10 grams of Dow D.E.N. 431, 19.04 grams of DENACOL EX-147 (Nagase ChemTex), and 2.01 grams Dow UVI-6976 were measured into a-125 mL, brown Nalgene bottle.
2. The components were combined on a mixing wheel for 72 hours at 50 rpm.
B. Preparation of Films From Formulation 20
Using normal spin-coating and UV-curing techniques, the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.). A CEE IOOCB
Spinner/Hotplate was used to apply Formulation 20 to wafers. The spin speed was 1,000- 5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 360 seconds.
A Canon PLA-501 F Parallel Light Mask Aligner with xenon lamp was used to cure the films. The output was 2.7 mJ-sec/cm2 at 365 nm, the time was 12 minutes, and the total exposure dose was 2 J/cm2.
Representative film processing data for these materials are shown in Table 39.
Table 39
The data of Table 40 were obtained through the analysis of the above films by using a prism coupler (Metricon 2010).
Table 40
The refractive index (n) and extinction coefficient (k) data (see Fig. 43) were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J. A.
Woollam Company).
The transmission data of the films, shown in the graph of Fig.44 and expressed as a percentage, were obtained using a Varian Gary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer. The mode used was nanometers, with a range of 300-3,300 nm. For
the scan controls, the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nrn/min. The Y mode parameters were Y min = 0.00, and Y max = 100.00. The baseline parameter was zeπVbaseline.
EXAMPLE 21
A Curable High Refractive Index Resin Prepared with a Brominated Epoxy Resin and an Epoxy Novolac Resin
A. Preparation of Formulation 21
The following procedure was used to prepare a curable high refractive index coating:
1. First, 43.35 grams of DENACOL EX-147 (Nagase ChemTex), 3.33 grams of EPIKOTE 157 (Resolution Performance Products ), and 3.76 grams DTS-102 (Midori Kagaku) were measured into a 125-mL, brown Nalgene bottle.
2. The components were combined on a mixing wheel for 96 hours at 50 rpm.
B. Preparation of Films From Formulation 21
Using normal spin-coating and UV-curing techniques, the formulation can be coated onto various types of wafers (silicon, quartz, glass, etc.). A CEE IOOCB Spinner/Hotplate was used to apply formulation 21 to wafers. The spin speed was 1 ,000- 5,000 rpm, the acceleration was 4,500 rpm/sec, and the spin time was 60 seconds.
A Canon PLA-50 IF Parallel Light Mask Aligner with xenon lamp was used to cure the films. The output was 2.7 mJ-sec/cm2 at 365 nm, the time was 6 minutes, and the total exposure dose was 1 J/cm2.
Representative film processing data for these materials are shown in Table 41.
Table 41
The data of Table 42 were obtained through the analysis of the above films by using a prism coupler (Metricon 2010).
Table 42
The refractive index (n) and extinction coefficient (Jc) data (See Fig. 45) were obtained using a variable angle spectroscopic ellipsometer (VASE, M2000 VASE, J.A. Woollam Company).
The transmission data of the films, shown in the graph of Fig.46 and expressed as a percentage, were obtained using a Varian Cary 500 Scan UV-Vis-NIR Dual Beam Spectrophotometer. The mode used was nanometers, with a range of 300-3,300 nm. For the scan controls, the average time was 0.1 second, the data interval was 1.0 nm, and the scan rate was 600 nm/min. The Y mode parameters were Y min = 0.00, and Y max = 100.00. The baseline parameter was zero/baseline.
Claims
1. A composition useful for fabricating optoelectronic components, said composition comprising a mixture of: a compound having a formula selected from the group consisting of
Aromatic R2 R
R,C :=C O- 1f Moiety I — o — c — c2 — o- Aromatic Moiety I — O C=CR2
, and
where: each R is individually selected from the group consisting of hydrogen, alkyls, alkoxys, cycloaliphatics, and aromatics; each B is individually selected from the group consisting of -CO-, -COO-, -CON-,-0-, -S-, -SO-, -SO2-, -CR2-, and -NR-; each Q is individually selected from the group consisting Of-CR2; each D is individually selected from the group consisting of -VCRCR2, where V is selected from the group consisting of -O- and -S-; each Z is individually selected from the group consisting of
x is from about 0-6; and n is from about O- 100; and a crosslinking catalyst, wherein said composition comprises less than about 5% by weight of non-reactive solvent, based upon the total weight of the composition taken as 100% by weight.
2. The composition of claim 1, wherein: each Aromatic Moiety I is individually selected from the group consisting of
each Aromatic Moiety II is individually selected from the group consisting of
each Aromatic Moiety III is individually selected from the group consisting of
where: each R is individually selected from the group consisting of -C(CR"'3)2-, -CR'"2-, -SO2-, -S-, -SO-, and -CO-, where each R'" is individually selected from the group consisting of hydrogen, alkyls, alkoxys, cycloaliphatics, and aromatics; each R" is individually selected from the group consisting of -CR'"2-,
-SO2-, -SO-, -S-, -O-, -CO-, and -NR'"-, where each R" is individually selected from the group consisting of hydrogen, alkyls, alkoxys, cycloaliphatics, and aromatics; each X is individually selected from the group consisting of the halogens; each m is individually selected from the group consisting of 0-6; and each y is individually selected from the group consisting of 0-6.
3. The composition of claim 2, where R is hydrogen.
4. The composition of claim 1 , said mixture further comprising a compound having a formula selected from the group consisting of
where: each R" is individually selected from the group consisting of -CR'"2-, -SO2-, -SO-, -S-, -O-, -CO-, and -NR1"-, where each R1" is individually selected from the group consisting of hydrogen, alkyls, alkoxys, cycloaliphatics, and aromatics; each X is individually selected from the group consisting of the halogens; each m is individually selected from the group consisting of 0-6; and each y is individually selected from the group consisting of 0-6.
5. The composition of claim 1 , wherein said crosslinking catalyst is selected from the group consisting of acids, photoacid generators, photobases, thermal acid generators, thermal base generators, and mixtures thereof.
6. A method of forming an optoelectronic component, said method comprising the step of applying a composition to a substrate so as to form a layer of said composition on said substrate, said composition comprising a mixture of: a compound having a formula selected from the group consisting of
where: each R is individually selected from the group consisting of hydrogen, alkyls, alkoxys, cycloaliphatics, and aromatics; each B is individually selected from the group consisting of -CO-, -COO-, -CON-,-0-, -S-, -SO-, -SO2-, -CR2-, and -NR-; each Q is individually selected from the group consisting Of-CR2; each D is individually selected from the group consisting of
-VCRCR2, where V is selected from the group consisting of
-O- and -S-; each Z is individually selected from the group consisting of
x is from about 0-6; and n is from about 0-100; and a crosslinking catalyst, wherein said composition comprises less than about 5% by weight of non-reactive solvent, based upon the total weight of the composition taken as 100% by weight.
7. The method of claim 6, wherein said substrate is selected from the group consisting of silicon, silicon dioxide, silicon nitride, aluminum gallium arsenide, aluminum indium gallium phosphide, gallium nitride, gallium arsenide, indium gallium phosphide, indium gallium nitride, indium gallium arsenide, aluminum oxide, glass, quartz, polycarbonates, polyesters, acrylics, polyurethanes, papers, ceramics, and metals.
8. The method of claim 6, further comprising the step of curing said layer.
9. The method of claim 8, wherein said curing step comprises heating said composition to a temperature of at least about 400C for at least about 5 seconds.
10. The method of claim 8, wherein said curing step comprises exposing said layer to light at a wavelength effective for curing said layer.
11. The method of claim 8, wherein said cured layer has a refractive index of at least about 1.5 at a wavelength of from about 375-1,700 nm.
12. The method of claim 8, wherein said cured layer has a percent transmittance of at least about 80% of light at a wavelengths of from about 375-1 ,700 nm and at a film thickness of about 100 μm.
13. The method of claim 6, wherein: each Aromatic Moiety I is individually selected from the group consisting of
each Aromatic Moiety II is individually selected from the group consisting of
each Aromatic Moiety III is individually selected from the group consisting of
where: each R' is individually selected from the group consisting of -C(CR"'3)2-, , -CR'"2-, -SO2-, -S-, -SO-, and -CO-, where each R'" is individually selected from the group consisting of hydrogen, alkyls, alkoxys, cycloaliphatics, and aromatics; each R" is individually selected from the group consisting of -CR'"2-,
-SO2-, -SO-, -S-, -O-, -CO-, and -NR"1-, where each R'" is individually selected from the group consisting of hydrogen, alkyls, alkoxys, cycloaliphatics, and aromatics; each X is individually selected from the group consisting of the halogens; each m is individually selected from the group consisting of 0-6; and each y is individually selected from the group consisting of 0-6.
14. The method of claim 13, where R is hydrogen.
15. The method of claim 6, said mixture further comprising a compound having a formula selected from the group consisting of
where: each R" is individually selected from the group consisting of -CR'"2-, -SO2-, -SO-, -S-, -O-, -CO-, and -NR"'-, where each R"' is individually selected from the group consisting of hydrogen, alkyls, alkoxys, cycloaliphatics, and aromatics; each X is individually selected from the group consisting of the halogens; each m is individually selected from the group consisting of 0-6; and each y is individually selected from the group consisting of 0-6.
16. The method of claim 6, wherein said crosslinking catalyst is selected from the group consisting of acids, photoacid generators, photobases, thermal acid generators, thermal base generators, and mixtures thereof.
17. A method of forming an optoelectronic component, said method comprising the step of applying a composition to a substrate so as to form a layer of said composition on said substrate; said composition comprising a compound having a formula selected from the group consisting of
Aromatic R2 R2 Aromatic
R9C= -o- Moiety I — O C C O- Moiety I
, and
where: each R is individually selected from the group consisting of hydrogen, alkyls, alkoxys, cycloaliphatics, and aromatics; each B is individually selected from the group consisting of -CO-, -COO-, -CON-,-0-, -S-, -SO-, -SO2-, -CR2-, and -NR-; each Q is individually selected from the group consisting Of-CR2; each D is individually selected from the group consisting of -VCRCR2, where V is selected from the group consisting of -O- and -S-; each Z is individually selected from the group consisting of
x is from about 0-6; and n is from about 0-100; and said substrate being selected from the group consisting of silicon, silicon dioxide, silicon nitride, aluminum gallium arsenide, aluminum indium gallium phosphide, gallium nitride, gallium arsenide, indium gallium phosphide, indium gallium nitride, indium gallium arsenide, aluminum oxide, glass, quartz, polycarbonates, polyesters, acrylics, polyurethanes, papers, ceramics, and metals.
18. The method of claim 17, further comprising the step of curing said layer.
19. The method of claim 18, wherein said curing step comprises heating said composition to a temperature of at least about 40° C for at least about 5 seconds.
20. The method of claim 18, wherein said curing step comprises exposing said layer to light at a wavelength effective for curing said layer.
21. The method of claim 18, wherein said cured layer has a refractive index of at least about 1.5 at a wavelength of from about 375-1,700 nm.
22. The method of claim 18, wherein said cured layer has a percent transmittance of at least about 80% of light at a wavelengths of from about 375-1,700 nm and at a film thickness of about 100 um.
23. The method of claim 17, said composition further comprising a crosslinking catalyst.
24. The method of claim 23 , wherein said crosslinking catalyst is selected from the group consisting of acids, photoacid generators, photobases, thermal acid generators, thermal base generators, and mixtures thereof.
25. The method of claim 17, wherein said composition comprises less than about 5% by weight of non-reactive solvent, based upon the total weight of the composition taken as 100% by weight.
26. The method of claim 17, wherein: each Aromatic Moiety I is individually selected from the group consisting of
each Aromatic Moiety II is individually selected from the group consisting of
each Aromatic Moiety III is individually selected from the group consisting of
where: each R' is individually selected from the group consisting of -C(CR"'3)2-, -CR'"2-, -SO2-, -S-, -SO-, and -CO-, where each R'" is individually selected from the group consisting of hydrogen, alkyls, alkoxys, cycloaliphatics, and aromatics; each R" is individually selected from the group consisting of -CR'"2-,
-SO2-, -SO-, -S-, -0-, -CO-, and -NR'"-, where each R"' is individually selected from the group consisting of hydrogen, alkyls, alkoxys, cycloaliphatics, and aromatics; each X is individually selected from the group consisting of the halogens; each m is individually selected from the group consisting of 0-6; and each y is individually selected from the group consisting of 0-6.
27. The method of claim 17, where R is hydrogen.
28. The method of claim 17, said mixture further comprising a compound having a formula selected from the group consisting of
where: each R" is individually selected from the group consisting of -CR'"2-, -SO2-, -SO-, -S-, -O-, -CO-, and -NR'"-, where each R1" is individually selected from the group consisting of hydrogen, alkyls, alkoxys, cycloaliphatics, and aromatics; each X is individually selected from the group consisting of the halogens; each m is individually selected from the group consisting of 0-6; and each y is individually selected from the group consisting of 0-6.
29. The combination of: a substrate having a surface; and a layer of a composition on said substrate surface, said composition comprising a mixture of: a compound having a formula selected from the group consisting of
o OR
/ \ R2 , I Aromatic R2 Ko Aromatic R2
R 2 C-C-C-OiJ Moiety I 1 — O C-
R -0V Moiety I I — O C C Λ CR2
R
where: each R is individually selected from the group consisting of hydrogen, alkyls, alkoxys, cycloaliphatics, and aromatics; each B is individually selected from the group consisting of -CO-, -COO-, -CON-,-0-, -S-, -SO-, -SO2-, -CR2-, and -NR-; each Q is individually selected from the group consisting Of-CR2; each D is individually selected from the group consisting of -VCRCR2, where V is selected from the group consisting of -O- and -S-; each Z is individually selected from the group consisting of
x is from about 0-6; and n is from about 0-100; and a crosslinking catalyst, wherein said composition comprises less than about 5% by weight of non- reactive solvent, based upon the total weight of the composition taken as 100% by weight.
30. The combination of claim 29, wherein said substrate is selected from the group consisting of silicon, silicon dioxide, silicon nitride, aluminum gallium arsenide, aluminum indium gallium phosphide, gallium nitride, gallium arsenide, indium gallium phosphide, indium gallium nitride, indium gallium arsenide, aluminum oxide, glass, quartz, polycarbonates, polyesters, acrylics, polyurethanes, papers, ceramics, and metals.
31. The combination of claim 29, wherein each aromatic moiety is individually selected from the group consisting of wherein: each Aromatic Moiety I is individually selected from the group consisting of
each Aromatic Moiety II is individually selected from the group consisting of
each Aromatic Moiety III is individually selected from the group consisting of
where: each R' is individually selected from the group consisting of -C(CR'"3)2-, -CR'"2-, -SO2-, -S-, -SO-, and -CO-, where each R'" is individually selected from the group consisting of hydrogen, alkyls, alkoxys, cycloaliphatics, and aromatics; each R" is individually selected from the group consisting of -CR'"2-,
-SO2-, -SO-, -S-, -0-, -CO-, and -NR1"-, where each R" is individually selected from the group consisting of hydrogen, alkyls, alkoxys, cycloaliphatics, and aromatics; each X is individually selected from the group consisting of the halogens; each m is individually selected from the group consisting of 0-6; and each y is individually selected from the group consisting of 0-6.
32. The combination of: a substrate having a surface; and a layer of a composition on said substrate surface, said composition comprising a compound having a formula selected from the group consisting of
where: each R is individually selected from the group consisting of hydrogen, alkyls, alkoxys, cycloaliphatics, and aromatics; 19 each B is individually selected from the group consisting of -CO-, -COO-, -CON-,-O-, -S-, -SO-, -SO2-, -CR2-, and -NR-; each Q is individually selected from the group consisting Of-CR2; each D is individually selected from the group consisting of -VCRCR2, where V is selected from the group consisting of -O- and -S-; each Z is individually selected from the group consisting of
x is from about 0-6; and n is from about 0-100; and said substrate being selected from the group consisting of silicon, silicon dioxide, silicon nitride, aluminum gallium arsenide, aluminum indium gallium phosphide, gallium nitride, gallium arsenide, indium gallium phosphide, indium gallium nitride, indium gallium arsenide, aluminum oxide, glass, quartz, polycarbonates, polyesters, acrylics, polyurethanes, papers, ceramics, and metals.
33. The combination of claim 32, said composition further comprising a crosslinking catalyst.
34. The combination of claim 33, wherein said crosslinking catalyst is selected from the group consisting of acids, photoacid generators, photobases, thermal acid generators, thermal base generators, and mixtures thereof.
35. The combination of claim 32, wherein said composition comprises less than about 5% by weight of non-reactive solvent, based upon the total weight of the composition taken as 100% by weight.
36. The combination of claim 32, wherein each aromatic moiety is individually selected from the group consisting of wherein: each Aromatic Moiety I is individually selected from the group consisting of
each Aromatic Moiety II is individually selected from the group consisting of
each Aromatic Moiety III is individually selected from the group consisting of
where: each R' is individually selected from the group consisting of -C(CR'"3)2-, -CR'"2-, -SO2-, -S-, -SO-, and -CO-, where each R1" is individually selected from the group consisting of hydrogen, alkyls, alkoxys, cycloaliphatics, and aromatics; each R" is individually selected from the group consisting of -CR'"2-,
-SO2-, -SO-, -S-, -0-, -CO-, and -NR"1-, where each R'" is individually selected from the group consisting of hydrogen, alkyls, alkoxys, cycloaliphatics, and aromatics; each X is individually selected from the group consisting of the halogens; each m is individually selected from the group consisting of 0-6; and each y is individually selected from the group consisting of 0-6.
37. The combination of: a substrate having a surface; and a cured layer of a composition on said substrate surface, said cured layer comprising crosslinked compounds having a formula selected from the group consisting of
where: each R is individually selected from the group consisting of hydrogen, alkyls, alkoxys, cycloaliphatics, and aromatics; and n is from about 0-100, said cured layer having a refractive index of at least about 1.5 at a wavelength of from about 375- 1 ,700 nm.
38. The combination of claim 37, said substrate being selected from the group consisting of silicon, silicon dioxide, silicon nitride, aluminum gallium arsenide, aluminum indium gallium phosphide, gallium nitride, gallium arsenide, indium gallium phosphide, indium gallium nitride, indium gallium arsenide, aluminum oxide, glass, quartz, polycarbonates, polyesters, acrylics, polyurethanes, papers, ceramics, and metals.
39. The combination of claim 37, wherein each aromatic moiety is individually selected from the group consisting of wherein: each Aromatic Moiety I is individually selected from the group consisting of
each Aromatic Moiety II is individually selected from the group consisting of
each Aromatic Moiety III is individually selected from the group consisting of
where: each R' is individually selected from the group consisting of -C(CR'"3)2-, -CR'"2-, -SO2-, -S-, -SO-, and -CO-, where each R1" is individually selected from the group consisting of hydrogen, alkyls, alkoxys, cycloaliphatics, and aromatics; each R" is individually selected from the group consisting of -CR'"2-, -SO2-, -SO-, -S-, -O-, -CO-, and -NR'"-, where each Rm is individually selected from the group consisting of hydrogen, alkyls, alkoxys, cycloaliphatics, and aromatics; each X is individually selected from the group consisting of the halogens; each m is individually selected from the group consisting of 0-6; and each y is individually selected from the group consisting of 0-6.
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- 2005-09-26 JP JP2007533680A patent/JP2008514764A/en active Pending
- 2005-09-26 CN CNA2005800323223A patent/CN101142499A/en active Pending
- 2005-09-26 US US11/235,619 patent/US20060068207A1/en not_active Abandoned
- 2005-09-26 EP EP20050858173 patent/EP1815273A2/en not_active Withdrawn
- 2005-09-26 KR KR1020057022451A patent/KR20070072939A/en not_active Application Discontinuation
- 2005-09-28 TW TW094133712A patent/TW200619312A/en unknown
-
2008
- 2008-08-19 US US12/194,369 patent/US20090087666A1/en not_active Abandoned
Non-Patent Citations (1)
Title |
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See references of WO2006137884A2 * |
Also Published As
Publication number | Publication date |
---|---|
CN101142499A (en) | 2008-03-12 |
US20090087666A1 (en) | 2009-04-02 |
JP2008514764A (en) | 2008-05-08 |
TW200619312A (en) | 2006-06-16 |
WO2006137884A2 (en) | 2006-12-28 |
KR20070072939A (en) | 2007-07-10 |
WO2006137884A3 (en) | 2007-06-28 |
US20060068207A1 (en) | 2006-03-30 |
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